Trifluoroacetic acid → 7-[2-Carboxymethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid

HRID 569416Notes

Reaction equation

HRID 569416 reaction equation
C([O:5][C:6]([CH2:8][O:9][N:10]=[C:11]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:12]([NH:14][CH:15]1[C:40](=[O:41])[N:17]2[C:18]([C:24]([O:26]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]12)=[O:13])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.C(Cl)Cl>[C:6]([CH2:8][O:9][N:10]=[C:11]([C:42]1[N:43]=[C:44]([NH:47][CH:48]=[O:49])[S:45][CH:46]=1)[C:12]([NH:14][CH:15]1[C:40](=[O:41])[N:17]2[C:18]([C:24]([OH:26])=[O:25])=[C:19]([CH:22]=[CH2:23])[CH2:20][S:21][C@H:16]12)=[O:13])([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131713176Benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)-acetamido]-3-vinyl-3-cephem-4-carboxylate

Product 1

HCID 1317131987-[2-Carboxymethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acidYield 91.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of benzhydryl 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylate (syn isomer) (2.5 g) in anisole (2.5 ml) and methylene chloride (5.0 ml) was added trifluoroacetic acid (10.0 ml) under ice-cooling, and the mixture was stirred at ambient temperature for 2 hours. To the reaction mixture was added dropwise diisopropyl ether, and the precipitated crystals were collected by filtration, washed with diisopropyl ether to obtain 7-[2-carboxymethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (1.57 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitated crystals were collected by filtration
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-b951cc33fd924fe7a51e60a7178a05a0
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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