NO762440L

NO762440L -

Info

Publication number: NO762440L
Authority: NO; Norway
Prior art keywords: group; phenyl; lower alkyl; acetic acid; cycloalkyl
Prior art date: 1972-12-22

Application number

NO762440A

Other languages

English (en)

Norwegian (no)

Inventor

R Heijboer

A Van Harrewijn

P W Henninger

Original Assignee

Gist Brocades Nv

Priority date

1972-12-22

Filing date

1976-07-12

Publication date

1974-06-25

1972-12-22 Priority claimed from GB5952472A external-priority patent/GB1459392A/en

1974-06-25 Publication of NO762440L publication Critical patent/NO762440L/no

1976-07-12 Application filed by Gist Brocades Nv filed Critical Gist Brocades Nv

1976-07-12 Priority to NO762440A priority Critical patent/NO762440L/no

Links

150000001875 compounds Chemical class 0.000 claims description 97
125000000217 alkyl group Chemical group 0.000 claims description 77
-1 isothiozolyl Chemical group 0.000 claims description 73
238000006243 chemical reaction Methods 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 65
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 63
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
238000000034 method Methods 0.000 claims description 61
238000002360 preparation method Methods 0.000 claims description 53
125000000753 cycloalkyl group Chemical group 0.000 claims description 42
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 36
125000001424 substituent group Chemical group 0.000 claims description 30
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
150000007513 acids Chemical class 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 20
239000001569 carbon dioxide Substances 0.000 claims description 18
229910002092 carbon dioxide Inorganic materials 0.000 claims description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 17
SPLXTCXODDVKKW-UHFFFAOYSA-N 2-(3-methyl-1,2,4-oxadiazol-5-yl)acetic acid Chemical compound CC1=NOC(CC(O)=O)=N1 SPLXTCXODDVKKW-UHFFFAOYSA-N 0.000 claims description 16
125000003710 aryl alkyl group Chemical group 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
WBDQZHONDVMBJO-UHFFFAOYSA-N 2-(1,2,4-oxadiazol-3-yl)acetic acid Chemical class OC(=O)CC=1N=CON=1 WBDQZHONDVMBJO-UHFFFAOYSA-N 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
230000000694 effects Effects 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
150000002825 nitriles Chemical class 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 7
238000001816 cooling Methods 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
150000008065 acid anhydrides Chemical class 0.000 claims description 5
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims description 4
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
KENPOHOXFDQEPU-UHFFFAOYSA-N 2-(3-ethyl-1,2,4-oxadiazol-5-yl)propanoic acid Chemical compound CCC1=NOC(C(C)C(O)=O)=N1 KENPOHOXFDQEPU-UHFFFAOYSA-N 0.000 claims description 3
AHKRYBQOKJFZTJ-UHFFFAOYSA-N 2-(5-ethyl-1,2,4-oxadiazol-3-yl)acetic acid Chemical compound CCC1=NC(CC(O)=O)=NO1 AHKRYBQOKJFZTJ-UHFFFAOYSA-N 0.000 claims description 3
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 3
125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
125000003107 substituted aryl group Chemical group 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
YZMYSOVWUBONMM-UHFFFAOYSA-N 2-(5-benzyl-1,2,4-oxadiazol-3-yl)acetic acid Chemical compound OC(=O)CC1=NOC(CC=2C=CC=CC=2)=N1 YZMYSOVWUBONMM-UHFFFAOYSA-N 0.000 claims description 2
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 9
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
125000004185 ester group Chemical group 0.000 claims 2
GIIIZOIAVVQNOF-UHFFFAOYSA-N 2-[3-(2,4,6-trimethylphenyl)-1,2,4-oxadiazol-5-yl]acetic acid Chemical compound CC1=CC(C)=CC(C)=C1C1=NOC(CC(O)=O)=N1 GIIIZOIAVVQNOF-UHFFFAOYSA-N 0.000 claims 1
SYRIGWYHNNKJHH-UHFFFAOYSA-N 2-[3-(hydroxymethyl)-1,2,4-oxadiazol-5-yl]acetic acid Chemical compound OCC1=NOC(CC(O)=O)=N1 SYRIGWYHNNKJHH-UHFFFAOYSA-N 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
238000003763 carbonization Methods 0.000 claims 1
238000006798 ring closing metathesis reaction Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 222
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 221
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 135
239000000243 solution Substances 0.000 description 122
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
239000000203 mixture Substances 0.000 description 105
239000010410 layer Substances 0.000 description 96
239000000047 product Substances 0.000 description 81
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 60
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 52
239000011541 reaction mixture Substances 0.000 description 51
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
239000007787 solid Substances 0.000 description 44
238000002844 melting Methods 0.000 description 38
230000008018 melting Effects 0.000 description 38
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 36
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 33
239000012044 organic layer Substances 0.000 description 32
239000000284 extract Substances 0.000 description 30
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 30
238000000605 extraction Methods 0.000 description 29
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
239000012948 isocyanate Substances 0.000 description 23
229910052708 sodium Inorganic materials 0.000 description 22
239000011734 sodium Substances 0.000 description 22
238000001228 spectrum Methods 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
239000005457 ice water Substances 0.000 description 21
150000002513 isocyanates Chemical class 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
230000009102 absorption Effects 0.000 description 20
238000010521 absorption reaction Methods 0.000 description 20
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
229930182555 Penicillin Natural products 0.000 description 17
238000001914 filtration Methods 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 14
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
150000001408 amides Chemical class 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
238000002955 isolation Methods 0.000 description 14
229940124587 cephalosporin Drugs 0.000 description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
229930186147 Cephalosporin Natural products 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
150000001780 cephalosporins Chemical class 0.000 description 12
239000003795 chemical substances by application Substances 0.000 description 12
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 12
229910052744 lithium Inorganic materials 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 11
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound 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 11
238000006114 decarboxylation reaction Methods 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
239000012467 final product Substances 0.000 description 11
238000002329 infrared spectrum Methods 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
229940049954 penicillin Drugs 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
239000006227 byproduct Substances 0.000 description 10
YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 10
HNJOAIYFUCQZAA-UHFFFAOYSA-N 3,5-dimethyl-1,2,4-oxadiazole Chemical compound CC1=NOC(C)=N1 HNJOAIYFUCQZAA-UHFFFAOYSA-N 0.000 description 9
238000009835 boiling Methods 0.000 description 9
238000001035 drying Methods 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
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 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
235000011054 acetic acid Nutrition 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 8
238000001556 precipitation Methods 0.000 description 8
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
PXSGMGFLCWXLJN-UHFFFAOYSA-N 2-(5-methyl-1,2,4-oxadiazol-3-yl)acetic acid Chemical compound CC1=NC(CC(O)=O)=NO1 PXSGMGFLCWXLJN-UHFFFAOYSA-N 0.000 description 7
HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
150000003931 anilides Chemical class 0.000 description 7
229960000603 cefalotin Drugs 0.000 description 7
VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 7
239000012043 crude product Substances 0.000 description 7
239000013078 crystal Substances 0.000 description 7
239000007788 liquid Substances 0.000 description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
239000012258 stirred mixture Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
GGGZAEXSWFTPKJ-UHFFFAOYSA-N 2-(oxadiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CON=N1 GGGZAEXSWFTPKJ-UHFFFAOYSA-N 0.000 description 6
YOASLLAJDWCQOC-UHFFFAOYSA-N 4-methyl-4-silylpentane-1-sulfonic acid Chemical compound CC(C)([SiH3])CCCS(O)(=O)=O YOASLLAJDWCQOC-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
238000010790 dilution Methods 0.000 description 6
239000012895 dilution Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
230000036961 partial effect Effects 0.000 description 6
150000002960 penicillins Chemical class 0.000 description 6
239000012047 saturated solution Substances 0.000 description 6
238000000926 separation method Methods 0.000 description 6
239000005051 trimethylchlorosilane Substances 0.000 description 6
OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 5
ANYVFOJLQKTQKU-UHFFFAOYSA-N 2-[5-(carboxymethyl)-1,2,4-oxadiazol-3-yl]acetic acid Chemical compound OC(=O)CC1=NOC(CC(O)=O)=N1 ANYVFOJLQKTQKU-UHFFFAOYSA-N 0.000 description 5
239000003242 anti bacterial agent Substances 0.000 description 5
239000004202 carbamide Substances 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical group 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
244000005700 microbiome Species 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000012429 reaction media Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 4
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 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
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