NL8003891A - Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. - Google Patents
Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. Download PDFInfo
- Publication number
- NL8003891A NL8003891A NL8003891A NL8003891A NL8003891A NL 8003891 A NL8003891 A NL 8003891A NL 8003891 A NL8003891 A NL 8003891A NL 8003891 A NL8003891 A NL 8003891A NL 8003891 A NL8003891 A NL 8003891A
- Authority
- NL
- Netherlands
- Prior art keywords
- group
- mmol
- minutes
- trimethylsilyl
- hexamethyldisilazane
- Prior art date
Links
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 title claims description 173
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 17
- 150000002894 organic compounds Chemical class 0.000 title claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title description 24
- 150000001875 compounds Chemical class 0.000 title description 14
- 238000006884 silylation reaction Methods 0.000 title description 13
- 238000006555 catalytic reaction Methods 0.000 title description 3
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical group C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 67
- 229940081974 saccharin Drugs 0.000 claims description 66
- 235000019204 saccharin Nutrition 0.000 claims description 66
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 claims description 66
- 239000003054 catalyst Substances 0.000 claims description 44
- -1 trimethylsilylamino group Chemical group 0.000 claims description 23
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 7
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- DGZBRVOXGIVBLN-UHFFFAOYSA-N [(diphenoxyphosphorylamino)-phenoxyphosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)NP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 DGZBRVOXGIVBLN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- FGXOGRSGUNCHQL-UHFFFAOYSA-N 2,2,2-trichloro-n-dimethoxyphosphorylacetamide Chemical compound COP(=O)(OC)NC(=O)C(Cl)(Cl)Cl FGXOGRSGUNCHQL-UHFFFAOYSA-N 0.000 claims description 3
- UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical group OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 claims description 3
- QRFTXHFUNIFHST-UHFFFAOYSA-N 4,5,6,7-tetrabromoisoindole-1,3-dione Chemical compound BrC1=C(Br)C(Br)=C2C(=O)NC(=O)C2=C1Br QRFTXHFUNIFHST-UHFFFAOYSA-N 0.000 claims description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 3
- AYDOWLQVELNYEE-UHFFFAOYSA-N [dimethyl-(sulfamoylamino)silyl]methane Chemical compound C[Si](C)(C)NS(N)(=O)=O AYDOWLQVELNYEE-UHFFFAOYSA-N 0.000 claims description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 3
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 3
- SGJFNRQZMRIAJP-UHFFFAOYSA-N n-(4-methylphenyl)sulfonylbenzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1 SGJFNRQZMRIAJP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006227 trimethylsilylation reaction Methods 0.000 claims description 3
- SVWAHAPZUQYXGM-UHFFFAOYSA-N (4-oxo-3h-phthalazin-1-yl) benzoate Chemical compound N=1NC(=O)C2=CC=CC=C2C=1OC(=O)C1=CC=CC=C1 SVWAHAPZUQYXGM-UHFFFAOYSA-N 0.000 claims description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- APOAEMIYHVGWEZ-UHFFFAOYSA-N 4-chloroisoindole-1,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)NC2=O APOAEMIYHVGWEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 142
- 238000010992 reflux Methods 0.000 description 104
- 229910021529 ammonia Inorganic materials 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 50
- 238000002360 preparation method Methods 0.000 description 49
- 239000000203 mixture Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 44
- 238000006243 chemical reaction Methods 0.000 description 36
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000035484 reaction time Effects 0.000 description 10
- 238000004448 titration Methods 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 8
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 6
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- NVIAYEIXYQCDAN-HWZXHQHMSA-N (6r)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 NVIAYEIXYQCDAN-HWZXHQHMSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 4
- YUWVMABNHZEMGO-UHFFFAOYSA-N 1-trimethylsilylpyrrolidine-2,5-dione Chemical compound C[Si](C)(C)N1C(=O)CCC1=O YUWVMABNHZEMGO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- HSHGZXNAXBPPDL-IOJJLOCKSA-N (6r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(N)[C@@H]12 HSHGZXNAXBPPDL-IOJJLOCKSA-N 0.000 description 2
- FAEFDCDBPXCRKX-UHFFFAOYSA-N (sulfonylamino)phosphonic acid Chemical class OP(O)(=O)N=S(=O)=O FAEFDCDBPXCRKX-UHFFFAOYSA-N 0.000 description 2
- ASABUEJOVHOJSW-UHFFFAOYSA-N 2,2,2-trichloro-n-trimethylsilylacetamide Chemical compound C[Si](C)(C)NC(=O)C(Cl)(Cl)Cl ASABUEJOVHOJSW-UHFFFAOYSA-N 0.000 description 2
- KRIMXCDMVRMCTC-UHFFFAOYSA-N 2-methylhexan-2-ol Chemical compound CCCCC(C)(C)O KRIMXCDMVRMCTC-UHFFFAOYSA-N 0.000 description 2
- BYEOMMQCENPXKM-UHFFFAOYSA-N 3-hydroxy-2-(trimethylsilylamino)propanoic acid Chemical compound C[Si](C)(C)NC(CO)C(O)=O BYEOMMQCENPXKM-UHFFFAOYSA-N 0.000 description 2
- PHIMQSCHTGNBCG-UHFFFAOYSA-N 3-trimethylsilyl-1,3-oxazolidin-2-id-4-one Chemical compound C[Si](N1[CH-]OCC1=O)(C)C PHIMQSCHTGNBCG-UHFFFAOYSA-N 0.000 description 2
- XLSYAWHCTYEHRB-UHFFFAOYSA-N 4-nitro-n-trimethylsilylbenzamide Chemical compound C[Si](C)(C)NC(=O)C1=CC=C([N+]([O-])=O)C=C1 XLSYAWHCTYEHRB-UHFFFAOYSA-N 0.000 description 2
- ZESWUEBPRPGMTP-UHFFFAOYSA-N 4-nitrobenzamide Chemical compound NC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZESWUEBPRPGMTP-UHFFFAOYSA-N 0.000 description 2
- CPGPAVAKSZHMBP-UHFFFAOYSA-N 9-methylanthracene Chemical compound C1=CC=C2C(C)=C(C=CC=C3)C3=CC2=C1 CPGPAVAKSZHMBP-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 229930186147 Cephalosporin Chemical class 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 229930182555 Penicillin Chemical class 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 150000001780 cephalosporins Chemical class 0.000 description 2
- PGRDNHQIURCHPZ-UHFFFAOYSA-N cyclohexyloxy(trimethyl)silane Chemical compound C[Si](C)(C)OC1CCCCC1 PGRDNHQIURCHPZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- ASWTVWBPXCLXKJ-UHFFFAOYSA-N dodecoxy(trimethyl)silane Chemical compound CCCCCCCCCCCCO[Si](C)(C)C ASWTVWBPXCLXKJ-UHFFFAOYSA-N 0.000 description 2
- TYQSGJQIXZTWHI-UHFFFAOYSA-N ethyl 3-trimethylsilyloxybut-2-enoate Chemical compound CCOC(=O)C=C(C)O[Si](C)(C)C TYQSGJQIXZTWHI-UHFFFAOYSA-N 0.000 description 2
- ZBGWAJQUDSCDPB-UHFFFAOYSA-N n-(benzenesulfonyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ZBGWAJQUDSCDPB-UHFFFAOYSA-N 0.000 description 2
- LWFWUJCJKPUZLV-UHFFFAOYSA-N n-trimethylsilylacetamide Chemical compound CC(=O)N[Si](C)(C)C LWFWUJCJKPUZLV-UHFFFAOYSA-N 0.000 description 2
- BLUMSOONSFWPGU-UHFFFAOYSA-N n-trimethylsilylbenzamide Chemical compound C[Si](C)(C)NC(=O)C1=CC=CC=C1 BLUMSOONSFWPGU-UHFFFAOYSA-N 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- 150000003509 tertiary alcohols Chemical class 0.000 description 2
- MNMVKGDEKPPREK-UHFFFAOYSA-N trimethyl(prop-2-enoxy)silane Chemical compound C[Si](C)(C)OCC=C MNMVKGDEKPPREK-UHFFFAOYSA-N 0.000 description 2
- 239000005051 trimethylchlorosilane Substances 0.000 description 2
- PPKIIULXAHVFKK-UHFFFAOYSA-N (2-chloroacetyl)oxyphosphonamidic acid Chemical compound C(C(=O)OP(=O)(N)O)Cl PPKIIULXAHVFKK-UHFFFAOYSA-N 0.000 description 1
- CSZHCBOEEPVSDP-UHFFFAOYSA-N (2-nitro-N-(2,2,2-trichloroacetyl)anilino)phosphonic acid Chemical compound C1=CC=C(C(=C1)N(C(=O)C(Cl)(Cl)Cl)P(=O)(O)O)[N+](=O)[O-] CSZHCBOEEPVSDP-UHFFFAOYSA-N 0.000 description 1
- RHAUQSAFHWDJKH-ZJOUEHCJSA-N (3S,4S,5S)-1,3,4,5,6-pentahydroxy-1,1,3,4,5-pentakis(trimethylsilyl)hexan-2-one Chemical compound C[Si](C)(C)[C@@]([C@]([C@@](C(C(O)([Si](C)(C)C)[Si](C)(C)C)=O)(O)[Si](C)(C)C)(O)[Si](C)(C)C)(O)CO RHAUQSAFHWDJKH-ZJOUEHCJSA-N 0.000 description 1
- PHIMLNXVWFHTLQ-MYXBAGLQSA-N (6r)-3-methyl-5,8-dioxo-7-[(2-phenylacetyl)amino]-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2=O)C)C(O)=O)NC(=O)CC1=CC=CC=C1 PHIMLNXVWFHTLQ-MYXBAGLQSA-N 0.000 description 1
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 1
- MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 description 1
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 1
- ZVWJFSCKAIBVPB-UHFFFAOYSA-N 1-phenyl-2-trimethylsilylhydrazine Chemical compound C[Si](C)(C)NNC1=CC=CC=C1 ZVWJFSCKAIBVPB-UHFFFAOYSA-N 0.000 description 1
- RPVBFFYNFVTCBX-UHFFFAOYSA-N 1-trimethylsilylazepan-2-one Chemical compound C[Si](C)(C)N1CCCCCC1=O RPVBFFYNFVTCBX-UHFFFAOYSA-N 0.000 description 1
- REKDPEZNOOHVIP-UHFFFAOYSA-N 1-trimethylsilyloxypyrrolidine-2,5-dione Chemical compound C[Si](C)(C)ON1C(=O)CCC1=O REKDPEZNOOHVIP-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- JTTBJCQUBWXUHW-UHFFFAOYSA-N 2,2-dimethyl-n-trimethylsilylpropanamide Chemical compound CC(C)(C)C(=O)N[Si](C)(C)C JTTBJCQUBWXUHW-UHFFFAOYSA-N 0.000 description 1
- QARMHFWUIWEIOX-UHFFFAOYSA-N 2-methoxy-n-(4-methylphenyl)sulfonylnaphthalene-1-carboxamide Chemical compound COC1=CC=C2C=CC=CC2=C1C(=O)NS(=O)(=O)C1=CC=C(C)C=C1 QARMHFWUIWEIOX-UHFFFAOYSA-N 0.000 description 1
- ZRAPHEBMDYQXKR-UHFFFAOYSA-N 2-trimethylsilylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N([Si](C)(C)C)C(=O)C2=C1 ZRAPHEBMDYQXKR-UHFFFAOYSA-N 0.000 description 1
- HOUIVOGXYZMKES-UHFFFAOYSA-N 3-trimethylsilyloxycyclohex-2-en-1-one Chemical compound C[Si](C)(C)OC1=CC(=O)CCC1 HOUIVOGXYZMKES-UHFFFAOYSA-N 0.000 description 1
- LPUUYZVKCMCHLO-UHFFFAOYSA-N 4,5,6,7-tetrachloroisoindole-1,3-dione Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)NC(=O)C2=C1Cl LPUUYZVKCMCHLO-UHFFFAOYSA-N 0.000 description 1
- LHWZLUXODWUHLZ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)sulfonylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NS(=O)(=O)C1=CC=C(C)C=C1 LHWZLUXODWUHLZ-UHFFFAOYSA-N 0.000 description 1
- GKOGJMSMAQANGB-UHFFFAOYSA-N 4-methyl-n-trimethylsilylaniline Chemical compound CC1=CC=C(N[Si](C)(C)C)C=C1 GKOGJMSMAQANGB-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- HVLDAPARQYMXFQ-UHFFFAOYSA-N 5,5-dimethyl-1,3-bis(trimethylsilyl)imidazolidine-2,4-dione Chemical compound CC1(C)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O HVLDAPARQYMXFQ-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 238000006418 Brown reaction Methods 0.000 description 1
- NLPQUIVUAAJPBL-UHFFFAOYSA-N C[Si](C)(C)NS(=O)=O Chemical compound C[Si](C)(C)NS(=O)=O NLPQUIVUAAJPBL-UHFFFAOYSA-N 0.000 description 1
- LWYFOYIKXQAIDE-UHFFFAOYSA-N C[Si](N[Si](C)(C)C)(C)C.C(C)(CC)C1=C(O[Si](C)(C)C)C(=CC=C1)C(C)CC Chemical compound C[Si](N[Si](C)(C)C)(C)C.C(C)(CC)C1=C(O[Si](C)(C)C)C(=CC=C1)C(C)CC LWYFOYIKXQAIDE-UHFFFAOYSA-N 0.000 description 1
- RTBSHGIHUCAXLI-UHFFFAOYSA-N C[Si](N[Si](C)(C)C)(C)C.C[Si](NC(=O)OCC)(C)C Chemical compound C[Si](N[Si](C)(C)C)(C)C.C[Si](NC(=O)OCC)(C)C RTBSHGIHUCAXLI-UHFFFAOYSA-N 0.000 description 1
- QLMFBNPDVDOJKP-UHFFFAOYSA-N C[Si](N[Si](C)(C)C)(C)C.C[Si](NC(C)=S)(C)C Chemical compound C[Si](N[Si](C)(C)C)(C)C.C[Si](NC(C)=S)(C)C QLMFBNPDVDOJKP-UHFFFAOYSA-N 0.000 description 1
- UFVAESOOZCVJBY-UHFFFAOYSA-N C[Si](N[Si](C)(C)C)(C)C.C[Si](NC1=CC=C(C=C1)C)(C)C Chemical compound C[Si](N[Si](C)(C)C)(C)C.C[Si](NC1=CC=C(C=C1)C)(C)C UFVAESOOZCVJBY-UHFFFAOYSA-N 0.000 description 1
- MNAMGLKDGYEVLG-UHFFFAOYSA-N C[Si](N[Si](C)(C)C)(C)C.C[Si](NS(=O)(=O)C)(C)C Chemical compound C[Si](N[Si](C)(C)C)(C)C.C[Si](NS(=O)(=O)C)(C)C MNAMGLKDGYEVLG-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- HZQXZNMFRJJBFK-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane N-trimethylsilylbenzenesulfonamide Chemical compound C[Si](N[Si](C)(C)C)(C)C.C[Si](NS(=O)(=O)C1=CC=CC=C1)(C)C HZQXZNMFRJJBFK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical class 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- PXNYJNUWOLDIPO-UHFFFAOYSA-N hexan-2-yloxy(trimethyl)silane Chemical compound CCCCC(C)O[Si](C)(C)C PXNYJNUWOLDIPO-UHFFFAOYSA-N 0.000 description 1
- HNVBZKNIPZVUDV-UHFFFAOYSA-N hexoxy(trimethyl)silane Chemical compound CCCCCCO[Si](C)(C)C HNVBZKNIPZVUDV-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- QWMUDOFWQWBHFI-UHFFFAOYSA-N hydroxy-imino-diphenoxy-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=O)(N)OC1=CC=CC=C1 QWMUDOFWQWBHFI-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- UJXZOGCYFWARKH-UHFFFAOYSA-N n-trimethylsilylbenzenesulfonamide Chemical compound C[Si](C)(C)NS(=O)(=O)C1=CC=CC=C1 UJXZOGCYFWARKH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000008039 phosphoramides Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- OWJVJXSAWUDRAN-UHFFFAOYSA-N silyl benzoate Chemical compound [SiH3]OC(=O)C1=CC=CC=C1 OWJVJXSAWUDRAN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- WPSPBNRWECRRPK-UHFFFAOYSA-N trimethyl(1,2,4-triazol-1-yl)silane Chemical compound C[Si](C)(C)N1C=NC=N1 WPSPBNRWECRRPK-UHFFFAOYSA-N 0.000 description 1
- FAOKBCUOLAZFHY-UHFFFAOYSA-N trimethyl(2-methylbutan-2-yloxy)silane Chemical compound CCC(C)(C)O[Si](C)(C)C FAOKBCUOLAZFHY-UHFFFAOYSA-N 0.000 description 1
- DVSJVOTWXYADLD-UHFFFAOYSA-N trimethyl(2-methylhexan-2-yloxy)silane Chemical compound CCCCC(C)(C)O[Si](C)(C)C DVSJVOTWXYADLD-UHFFFAOYSA-N 0.000 description 1
- NYGJXYBYDZNXQY-UHFFFAOYSA-N trimethyl-(2-methylphenoxy)silane Chemical compound CC1=CC=CC=C1O[Si](C)(C)C NYGJXYBYDZNXQY-UHFFFAOYSA-N 0.000 description 1
- AVFDRQXHNKRWNG-FFFFSGIJSA-N trimethylsilyl (6r)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC(COC(=O)C)=C(C(=O)O[Si](C)(C)C)N2C(=O)C(N)[C@@H]12 AVFDRQXHNKRWNG-FFFFSGIJSA-N 0.000 description 1
- VFFKJOXNCSJSAQ-UHFFFAOYSA-N trimethylsilyl benzoate Chemical compound C[Si](C)(C)OC(=O)C1=CC=CC=C1 VFFKJOXNCSJSAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0801—General processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0898—Compounds with a Si-S linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1896—Compounds having one or more Si-O-acyl linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2479—Compounds containing the structure P(=X)n-N-acyl, P(=X)n-N-heteroatom, P(=X)n-N-CN (X = O, S, Se; n = 0, 1)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J51/00—Normal steroids with unmodified cyclopenta(a)hydrophenanthrene skeleton not provided for in groups C07J1/00 - C07J43/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8003891A NL8003891A (nl) | 1980-07-04 | 1980-07-04 | Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. |
| IL63100A IL63100A0 (en) | 1980-07-04 | 1981-06-15 | Trimethylsilylation of organic compounds and certain trimethylsilylated thiols obtained thereby |
| AU71886/81A AU543108B2 (en) | 1980-07-04 | 1981-06-16 | New catalysts for silylation |
| PT73261A PT73261B (en) | 1980-07-04 | 1981-06-25 | New catalysts for silylation |
| JP10312981A JPS5745192A (en) | 1980-07-04 | 1981-07-01 | Novel silylating catalyst |
| GR65410A GR74366B (enrdf_load_stackoverflow) | 1980-07-04 | 1981-07-02 | |
| FI812094A FI81776C (fi) | 1980-07-04 | 1981-07-02 | Foerfarande foer trimetylsilylering av organiska foereningar innehaollande en eller flera aktiva vaeteatomer medelst hexametyldisilazan. |
| AT81200771T ATE17353T1 (de) | 1980-07-04 | 1981-07-03 | Verfahren zum silylieren organischer verbindungen mit 1,1,1-trimethyl-n-(trimethylsilyl)silanamin mit hilfe von katalysatoren mit gewissen stickstoffhaltigen verbindungen. |
| EP81200771A EP0043630B1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| HU811958A HU185935B (en) | 1980-07-04 | 1981-07-03 | Process for sililizing organic materials with 1,1,1-trimethyl-n-bracket-trimethyl-silyl-bracket closed-silanamine in the presence of catalyty containing nitrogen |
| DE8181200771T DE3173428D1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| ES503650A ES8301485A1 (es) | 1980-07-04 | 1981-07-03 | Procedimiento para la trimetilsililacion de compuestos organicos que llevan uno o mas atomo de hidrogeno activo. |
| CA000381119A CA1184556A (en) | 1980-07-04 | 1981-07-03 | Catalysts for silylation |
| NO812275A NO812275L (no) | 1980-07-04 | 1981-07-03 | Fremgangsmaate for sililering av organiske forbindelser |
| DK296781A DK166581C (da) | 1980-07-04 | 1981-07-03 | Fremgangsmaade til trimethylsilylering af organiske forbindelser med hexamethyldisilazan i naervaerelse af en katalysator |
| IE1495/81A IE51452B1 (en) | 1980-07-04 | 1981-07-03 | Improved process for the silylation of organic compounds with 1,1,1-trimethyl-n-(trimethylsilyl)silanamine by means of catalysis with certain nitrogen containing compounds |
| US06/280,350 US4400509A (en) | 1980-07-04 | 1981-07-06 | Silylation process |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8003891 | 1980-07-04 | ||
| NL8003891A NL8003891A (nl) | 1980-07-04 | 1980-07-04 | Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8003891A true NL8003891A (nl) | 1982-02-01 |
Family
ID=19835569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8003891A NL8003891A (nl) | 1980-07-04 | 1980-07-04 | Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5745192A (enrdf_load_stackoverflow) |
| NL (1) | NL8003891A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS595194A (ja) * | 1982-06-30 | 1984-01-12 | Shin Etsu Chem Co Ltd | Ｎ，ｎ′−ビストリメチルシリル尿素の製造方法 |
-
1980
- 1980-07-04 NL NL8003891A patent/NL8003891A/nl not_active Application Discontinuation
-
1981
- 1981-07-01 JP JP10312981A patent/JPS5745192A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5745192A (en) | 1982-03-13 |
| JPS6361955B2 (enrdf_load_stackoverflow) | 1988-11-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Rassukana et al. | Fluorinated NH-iminophosphonates and iminocarboxylates: novel synthons for the preparation of biorelevant α-aminophosphonates and carboxylates | |
| FI81776B (fi) | Foerfarande foer trimetylsilylering av organiska foereningar innehaollande en eller flera aktiva vaeteatomer medelst hexametyldisilazan. | |
| CN112218868A (zh) | 三唑啉二酮加成物、三唑啉二酮加成物的制造方法、烯化合物的制造方法、及烯化合物的分析方法 | |
| NL8003891A (nl) | Verbeterde werkwijze voor de silylering van organische verbindingen met 1,1,1-trimethyl-n-(trimethylsilyl)- -silanamine door middel van katalyse met bepaalde stikstofbevattende verbindingen. | |
| US4412078A (en) | Hydantoinylsilanes | |
| Vieira et al. | Synthesis of potassium and tetra n-butylammonium 2-substituted-1, 3-dithianotrifluoroborate salts and addition to chiral cyclic N-acyliminium ions | |
| US20220009895A1 (en) | N-nitrosaccharins | |
| CN115197261B (zh) | 噁二氮杂硼衍生物的合成方法 | |
| Jois et al. | Synthesis of 2-cyano-1, 3-dibenzoyl-2, 3-dihydrobenzimidazole: a novel Reissert compound from benzimidazole | |
| US10947200B2 (en) | Substituted imidazolium sulfuranes and their use | |
| Sitzmann et al. | Novel route from thiocarbamate to isocyanate: 2, 2, 2-trinitroethyl isocyanate | |
| Kostyuk et al. | Structural sensitivity in phosphorylation of enamines—derivatives of β-aminocrotonic acid with diphenylchlorophosphine | |
| Di Terlizzi et al. | Aryl–Cl vs heteroatom–Si bond cleavage on the route to the photochemical generation of σ, π-heterodiradicals | |
| Petrik et al. | N-Bis (methylthio) methylene-trifluoromethanesulfonylamide CF3SO2N C (SCH3) 2: new reagent for the preparation of N-trifluoromethylsulfonylimino carbonic and thiocarbonic acids derivatives | |
| Zhang et al. | Reactivity and Diastereoselectivity in the Thermal and Lewis Acid-Catalyzed Diels− Alder Reactions of N-Sulfinylphosphoramidates1 | |
| CA2458859A1 (en) | (alpha)-haloenamine reagents | |
| KR840001213B1 (ko) | 특종의 촉매를 이용하는 유기화합물의 실릴화 방법 | |
| EP0280962B1 (en) | Process for preparing 4-acetoxy-3-hydroxyethylazetidin-2-one derivatives | |
| KR20130032561A (ko) | 아이오도벤젠 디아세테이트를 이용한 이미드 화합물의 제조방법 | |
| CA2986940A1 (en) | Industrial process for the preparation of enzalutamide | |
| Monfared et al. | A novel synthesis of functionalized sulfonamide derivatives using the reaction of substituted thiourea or oxime derivatives with N-(2, 3-dibromopropyl)-aryl (alkyl) sulfonamides | |
| JP4296266B2 (ja) | 新規なｎ−スルフェニル置換複素環化合物およびその製造方法 | |
| JPS5929049B2 (ja) | １，１，１−トリメトキシエタンの製造方法 | |
| JP4115692B2 (ja) | ２−スルホニルピリジン類の製造方法 | |
| Westwood et al. | An improved synthesis of trimethylsilylcyanide and its reaction with trimethylaluminium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |