Hydrochloric Acid → 7-[2-Carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid mono-hydrochloride

HRID 569429Notes

Reaction equation

HRID 569429 reaction equation
[ClH:1].C([O:6][C:7]([CH2:9][O:10][N:11]=[C:12]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:13]([NH:15][CH:16]1[C:41](=[O:42])[N:18]2[C:19]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:20]([CH:23]=[CH2:24])[CH2:21][S:22][C@H:17]12)=[O:14])=[O:8])(C)(C)C.C(OC(C)C)(C)C>C(O)=O>[ClH:1].[C:7]([CH2:9][O:10][N:11]=[C:12]([C:43]1[N:44]=[C:45]([NH2:48])[S:46][CH:47]=1)[C:13]([NH:15][CH:16]1[C:41](=[O:42])[N:18]2[C:19]([C:25]([OH:27])=[O:26])=[C:20]([CH:23]=[CH2:24])[CH2:21][S:22][C@H:17]12)=[O:14])([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7914Diisopropyl EtherHCID 131713177Benzhydryl 7-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 1317132147-[2-Carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid mono-hydrochlorideYield 73.6%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Conc. hydrochloric acid (0.18 g) was added to a solution of benzhydryl 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (3.0 g) in formic acid (12 ml) at 10° C. and stirred for 2.5 hours at ambient temperature. The reaction mixture was poured into diisopropyl ether (100 ml). The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid mono-hydrochloride (syn isomer) (1.6 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with diisopropyl ether
  3. customdried

Sources & evidence

ORD record
ord-fb0866810ebb44c7b721efa03a0e2cc6
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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