Trifluoroacetic acid → 7-[2-Carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 1463072노트

반응식

HRID 1463072 반응식
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:45]1[N:49]=[CH:48][S:47][N:46]=1)[C:19]([NH:21][CH:22]1[C:43](=[O:44])[N:24]2[C:25]([C:40]([OH:42])=[O:41])=[C:26]([CH2:29][S:30][C:31]3[CH:32]=[CH:33][C:34]4[N:35]([N:37]=[N:38][N:39]=4)[N:36]=3)[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:45]1[N:49]=[CH:48][S:47][N:46]=1)[C:19]([NH:21][CH:22]1[C:43](=[O:44])[N:24]2[C:25]([C:40]([OH:42])=[O:41])=[C:26]([CH2:29][S:30][C:31]3[CH:32]=[CH:33][C:34]4[N:35]([N:37]=[N:38][N:39]=4)[N:36]=3)[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

참가 물질

6

반응물 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 1317136127-[2-t-Butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid

생성물 1

HCID 1317136137-[2-Carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid수율 21.1%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7519Anisole용매

실험 절차

Trifluoroacetic acid (12 ml) was added to a suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (4 g) in methylene chloride (8 ml) and anisole (4 ml) at ambient temperature and the solution was stirred for 1.5 hours at the same temperature. To the resulting solution was added diisopropyl ether under stirring. The precipitates were collected by filtration, washed with diisopropyl ether. The precipitates were added to the mixture of ethyl acetate and water, and the mixture was adjusted to pH 7.5 with 20% aqueous solution of sodium carbonate. The separated aqueous layer was adjusted to pH 5.0 with 10% hydrochloric acid. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries Ltd.) and eluted with water. The fractions containing the object compound were adjusted to pH 2.0 with 10% hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide in vacuo to give 7-[2-carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]3-(tetrazolo[1,5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.77 g).

후처리

  1. stirringunder stirring
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with diisopropyl ether
  4. additionThe precipitates were added to the mixture of ethyl acetate and water
  5. custom" (Trademark: prepared by Mitsubishi Chemical Industries Ltd.)
  6. washeluted with water
  7. additionThe fractions containing the object compound
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with water
  10. dry with materialdried over phosphorus pentoxide in vacuo

출처 및 근거

ORD 기록
ord-2d198ced8de1485cb87b6793d5dfca98
출처 데이터셋
uspto-grants-1984_07
특허 번호
US04463003

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