CA1268183C

CA1268183C - Intermediaires du phosphorane utilises dans la preparation de penems antibiotiques

Intermediaires du phosphorane utilises dans la preparation de penems antibiotiques

Info

Publication number: CA1268183C
Authority: CA; Canada
Prior art keywords: alkyl; phenyl; alkylamino; heterocyclic; amino
Prior art date: 1978-12-18
Legal status : Expired

Application number

CA423146

Other languages

English (en)

Inventor

Marcel Menard

Alain Martel

Current Assignee

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Co

Priority date

1978-12-18

Filing date

1979-12-17

Publication date

1990-04-25

1979-12-17 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1990-04-25 Application granted granted Critical

1990-04-25 Publication of CA1268183C publication Critical patent/CA1268183C/fr

Status Expired legal-status Critical Current

Links

HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 title claims description 21
239000000543 intermediate Substances 0.000 title abstract description 19
VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 title abstract 2
239000003242 anti bacterial agent Substances 0.000 title description 3
230000003115 biocidal Effects 0.000 title description 2
229940064005 Antibiotic throat preparations Drugs 0.000 title 1
229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 title 1
229940042052 Antibiotics for systemic use Drugs 0.000 title 1
229940042786 Antitubercular Antibiotics Drugs 0.000 title 1
229940093922 Gynecological Antibiotics Drugs 0.000 title 1
229940024982 Topical Antifungal Antibiotics Drugs 0.000 title 1
229940079866 intestinal antibiotics Drugs 0.000 title 1
229940005935 ophthalmologic Antibiotics Drugs 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 198
150000001875 compounds Chemical class 0.000 claims abstract description 181
-1 hydroxyethyl Chemical group 0.000 claims abstract description 122
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 106
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 102
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 84
239000001257 hydrogen Substances 0.000 claims abstract description 57
125000001424 substituent group Chemical group 0.000 claims abstract description 35
125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract description 29
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 26
238000002360 preparation method Methods 0.000 claims abstract description 14
125000004185 ester group Chemical group 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 209
239000002253 acid Substances 0.000 claims description 85
238000000034 method Methods 0.000 claims description 81
125000000623 heterocyclic group Chemical class 0.000 claims description 70
125000003282 alkyl amino group Chemical group 0.000 claims description 59
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
125000003545 alkoxy group Chemical group 0.000 claims description 34
229910052757 nitrogen Inorganic materials 0.000 claims description 23
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 21
125000001931 aliphatic group Chemical group 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 11
125000005236 alkanoylamino group Chemical group 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000005466 alkylenyl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 4
JPVYNHNXODAKFH-UHFFFAOYSA-N cu2+ Chemical group [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 4
BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical compound [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 claims description 4
229910004664 ORa Inorganic materials 0.000 claims description 3
229910004727 OSO3H Inorganic materials 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
229910004755 ORb Inorganic materials 0.000 claims 2
229910006074 SO2NH2 Inorganic materials 0.000 claims 2
229910006069 SO3H Inorganic materials 0.000 claims 2
239000011780 sodium chloride Substances 0.000 abstract description 46
150000003839 salts Chemical class 0.000 abstract description 42
150000002961 penems Chemical class 0.000 abstract description 11
230000003389 potentiating Effects 0.000 abstract description 4
230000000844 anti-bacterial Effects 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 427
239000000243 solution Substances 0.000 description 349
239000000203 mixture Substances 0.000 description 249
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 227
229910001868 water Inorganic materials 0.000 description 218
XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 211
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 180
YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 179
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 170
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 159
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 118
239000007787 solid Substances 0.000 description 114
UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 109
239000012267 brine Substances 0.000 description 109
VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 95
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 86
239000003921 oil Substances 0.000 description 80
235000019198 oils Nutrition 0.000 description 80
229910000030 sodium bicarbonate Inorganic materials 0.000 description 76
235000019439 ethyl acetate Nutrition 0.000 description 74
239000011541 reaction mixture Substances 0.000 description 65
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 65
150000002148 esters Chemical group 0.000 description 63
239000002904 solvent Substances 0.000 description 62
239000000741 silica gel Substances 0.000 description 61
229910002027 silica gel Inorganic materials 0.000 description 61
229960001866 silicon dioxide Drugs 0.000 description 61
229940093499 ethyl acetate Drugs 0.000 description 60
230000035969 Vmax Effects 0.000 description 55
CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 51
235000017557 sodium bicarbonate Nutrition 0.000 description 51
239000000047 product Substances 0.000 description 50
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 49
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(I) nitrate Inorganic materials [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 49
125000003118 aryl group Chemical group 0.000 description 48
229910000041 hydrogen chloride Inorganic materials 0.000 description 48
229910052943 magnesium sulfate Inorganic materials 0.000 description 48
RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 47
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 47
238000006243 chemical reaction Methods 0.000 description 46
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 46
238000001704 evaporation Methods 0.000 description 42
239000000460 chlorine Substances 0.000 description 41
229910052709 silver Inorganic materials 0.000 description 41
239000004332 silver Substances 0.000 description 41
239000011734 sodium Substances 0.000 description 40
FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 38
239000000706 filtrate Substances 0.000 description 38
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 38
BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 38
238000003756 stirring Methods 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
239000002585 base Substances 0.000 description 33
UAOMVDZJSHZZME-UHFFFAOYSA-N Diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
239000010410 layer Substances 0.000 description 29
PXIPVTKHYLBLMZ-UHFFFAOYSA-N sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 29
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 28
238000010992 reflux Methods 0.000 description 28
238000001914 filtration Methods 0.000 description 26
235000019341 magnesium sulphate Nutrition 0.000 description 26
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 26
239000000377 silicon dioxide Substances 0.000 description 25
229940086542 triethylamine Drugs 0.000 description 25
229960001407 sodium bicarbonate Drugs 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000008079 hexane Substances 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
238000007792 addition Methods 0.000 description 21
239000000284 extract Substances 0.000 description 21
229910052708 sodium Inorganic materials 0.000 description 21
MNFORVFSTILPAW-UHFFFAOYSA-N Β-Lactam Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 21
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
ZCSHNCUQKCANBX-UHFFFAOYSA-N Lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 19
IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical group CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 19
239000003610 charcoal Substances 0.000 description 19
229910052681 coesite Inorganic materials 0.000 description 19
229910052906 cristobalite Inorganic materials 0.000 description 19
229910052904 quartz Inorganic materials 0.000 description 19
235000012239 silicon dioxide Nutrition 0.000 description 19
229910052682 stishovite Inorganic materials 0.000 description 19
229910052905 tridymite Inorganic materials 0.000 description 19
239000003054 catalyst Substances 0.000 description 18
229910052938 sodium sulfate Inorganic materials 0.000 description 18
235000011152 sodium sulphate Nutrition 0.000 description 18
239000007858 starting material Substances 0.000 description 18
229910052799 carbon Inorganic materials 0.000 description 17
238000004440 column chromatography Methods 0.000 description 17
238000000746 purification Methods 0.000 description 17
239000012346 acetyl chloride Substances 0.000 description 16
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 16
239000003480 eluent Substances 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
NLXLAEXVIDQMFP-UHFFFAOYSA-N ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
229940043279 diisopropylamine Drugs 0.000 description 15
239000006260 foam Substances 0.000 description 15
125000005843 halogen group Chemical group 0.000 description 15
OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
238000000935 solvent evaporation Methods 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
125000004432 carbon atoms Chemical group C* 0.000 description 14
238000002425 crystallisation Methods 0.000 description 14
230000005712 crystallization Effects 0.000 description 14
239000000463 material Substances 0.000 description 14
239000012299 nitrogen atmosphere Substances 0.000 description 14
229910052763 palladium Inorganic materials 0.000 description 14
239000000725 suspension Substances 0.000 description 14
WRJWRGBVPUUDLA-UHFFFAOYSA-N Chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 13
GNOIPBMMFNIUFM-UHFFFAOYSA-N Hexamethylphosphoramide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 13
238000001816 cooling Methods 0.000 description 13
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 13
HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminum hydride Chemical compound [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
239000002808 molecular sieve Substances 0.000 description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
229910001961 silver nitrate Inorganic materials 0.000 description 13
KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
ZCTHWZKWCUEIHN-UHFFFAOYSA-N 4-tritylsulfanylazetidin-2-one Chemical compound N1C(=O)CC1SC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZCTHWZKWCUEIHN-UHFFFAOYSA-N 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000007832 Na2SO4 Substances 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
101710027499 Os03g0268000 Proteins 0.000 description 11
238000001035 drying Methods 0.000 description 11
239000006188 syrup Substances 0.000 description 11
235000020357 syrup Nutrition 0.000 description 11
WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
235000019270 ammonium chloride Nutrition 0.000 description 10
HHLFWLYXYJOTON-UHFFFAOYSA-M glyoxylate Chemical compound [O-]C(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-M 0.000 description 10
238000005917 acylation reaction Methods 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 9
239000000843 powder Substances 0.000 description 9
BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 9
150000001450 anions Chemical class 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
229910052744 lithium Inorganic materials 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
239000012071 phase Substances 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
239000000538 analytical sample Substances 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
230000000875 corresponding Effects 0.000 description 7
239000012039 electrophile Substances 0.000 description 7
238000010828 elution Methods 0.000 description 7
238000005755 formation reaction Methods 0.000 description 7
WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 7
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
239000011591 potassium Substances 0.000 description 7
229910052700 potassium Inorganic materials 0.000 description 7
159000000000 sodium salts Chemical class 0.000 description 7
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
HVRMNEPIBIGCNZ-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-oxoacetate Chemical compound [O-][N+](=O)C1=CC=C(COC(=O)C=O)C=C1 HVRMNEPIBIGCNZ-UHFFFAOYSA-N 0.000 description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
AGPKZVBTJJNPAG-CRCLSJGQSA-N D-allo-isoleucine Chemical compound CC[C@H](C)[C@@H](N)C(O)=O AGPKZVBTJJNPAG-CRCLSJGQSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N Imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
125000004423 acyloxy group Chemical group 0.000 description 6
239000007864 aqueous solution Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 6
238000010348 incorporation Methods 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000012044 organic layer Substances 0.000 description 6
UKNAYQWNMMGCNX-UHFFFAOYSA-N sodium;[hydroxy(phenyl)methyl]-oxido-oxophosphanium Chemical compound [Na+].[O-][P+](=O)C(O)C1=CC=CC=C1 UKNAYQWNMMGCNX-UHFFFAOYSA-N 0.000 description 6
238000005406 washing Methods 0.000 description 6
MNVCCKVPSGWSCN-RXMQYKEDSA-N (5R)-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C(C)=C(C(O)=O)N2C(=O)C[C@H]21 MNVCCKVPSGWSCN-RXMQYKEDSA-N 0.000 description 5
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical class CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 5
SUHXTVABLHHRST-UHFFFAOYSA-N 2-azidoacetyl chloride Chemical compound ClC(=O)CN=[N+]=[N-] SUHXTVABLHHRST-UHFFFAOYSA-N 0.000 description 5
241000287523 Ara Species 0.000 description 5
239000005909 Kieselgur Substances 0.000 description 5
IJOOHPMOJXWVHK-UHFFFAOYSA-N Trimethylsilyl chloride Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
235000011089 carbon dioxide Nutrition 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N deuterated chloroform Substances [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
239000000499 gel Substances 0.000 description 5
238000000926 separation method Methods 0.000 description 5
YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 5
OEYMQQDJCUHKQS-UHFFFAOYSA-N (4-oxoazetidin-2-yl) acetate Chemical compound CC(=O)OC1CC(=O)N1 OEYMQQDJCUHKQS-UHFFFAOYSA-N 0.000 description 4
DWDDFMFCVGDERN-UHFFFAOYSA-N 1-chloroazetidin-2-one Chemical compound ClN1CCC1=O DWDDFMFCVGDERN-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Carbodicyclohexylimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
101700037397 MAX2 Proteins 0.000 description 4
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150000008041 alkali metal carbonates Chemical class 0.000 description 1
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229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
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150000003973 alkyl amines Chemical class 0.000 description 1
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229910052782 aluminium Inorganic materials 0.000 description 1
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150000001408 amides Chemical class 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
IMNRJGSQCGFPHL-UHFFFAOYSA-N benzene;oxolane Chemical compound C1CCOC1.C1=CC=CC=C1 IMNRJGSQCGFPHL-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
239000003782 beta lactam antibiotic agent Substances 0.000 description 1
125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DNSISZSEWVHGLH-UHFFFAOYSA-M butanimidate Chemical compound CCCC([NH-])=O DNSISZSEWVHGLH-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
235000012970 cakes Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000099 calcium monohydride Inorganic materials 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-M caproate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
XTEGARKTQYYJKE-UHFFFAOYSA-M chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
229940005991 chloric acid Drugs 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
125000002340 chlorooxy group Chemical group ClO[*] 0.000 description 1
AQIXAKUUQRKLND-UHFFFAOYSA-N cimetidine Chemical compound N#C/N=C(/NC)NCCSCC=1N=CNC=1C AQIXAKUUQRKLND-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
PEMWUGPZTRDXFZ-UHFFFAOYSA-N cyclohexa-1,4-diyne Chemical group C1C#C[C+]C#C1 PEMWUGPZTRDXFZ-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000003247 decreasing Effects 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
230000001419 dependent Effects 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000007865 diluting Methods 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
WXQSFECXTRCYSG-UHFFFAOYSA-N dimethyl-[methyl(trimethylsilyl)amino]silicon;lithium Chemical compound [Li].C[Si](C)N(C)[Si](C)(C)C WXQSFECXTRCYSG-UHFFFAOYSA-N 0.000 description 1
ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
238000006266 etherification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatoms Chemical group 0.000 description 1
150000004677 hydrates Chemical group 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;O-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
125000006289 hydroxybenzyl group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxyl anion Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007530 organic bases Chemical group 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000006303 photolysis reaction Methods 0.000 description 1
230000015843 photosynthesis, light reaction Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
238000004237 preparative chromatography Methods 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
VHWJSJBTUWUEAL-UHFFFAOYSA-N propanamide;hydrochloride Chemical compound Cl.CCC(N)=O VHWJSJBTUWUEAL-UHFFFAOYSA-N 0.000 description 1
230000002633 protecting Effects 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching Effects 0.000 description 1
239000003638 reducing agent Substances 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
150000003378 silver Chemical class 0.000 description 1
239000001187 sodium carbonate Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
VWMRHWQOUZWXNN-UHFFFAOYSA-M sodium;5-methyl-1,3-thiazole-4-carboxylate Chemical compound [Na+].CC=1SC=NC=1C([O-])=O VWMRHWQOUZWXNN-UHFFFAOYSA-M 0.000 description 1
NCFTXMQPRQZFMZ-UHFFFAOYSA-M sodium;7-[[2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)NC(C=1C=CC(O)=CC=1)C(=O)NC1C(=O)N2C(C([O-])=O)=C(CSC=3N(N=NN=3)C)CSC21 NCFTXMQPRQZFMZ-UHFFFAOYSA-M 0.000 description 1
ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 1
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
230000002194 synthesizing Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000017105 transposition Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000006000 trichloroethyl group Chemical group 0.000 description 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical group CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
238000005866 tritylation reaction Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1

CA423146 1978-12-18 1979-12-17 Intermediaires du phosphorane utilises dans la preparation de penems antibiotiques Expired CA1268183C (fr)