Trifluoroacetic acid → 7-[2-Carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-cephem-4-carboxylic acid
Reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:34]1[N:38]=[CH:37][S:36][N:35]=1)[C:19]([NH:21][CH:22]1[C:32](=[O:33])[N:24]2[C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:34]1[N:38]=[CH:37][S:36][N:35]=1)[C:19]([NH:21][CH:22]1[C:32](=[O:33])[N:24]2[C:25]([C:29]([OH:31])=[O:30])=[CH:26][CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Trifluoroacetic acid (3.6 ml) was added to a suspension of 7-[2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.2 g) in anisole (1.2 ml), and the mixture was stirred for 2 hours at ambient temperature. The resultant solution was added dropwise to diisopropyl ether (100 ml) and the precipitates were collected by filtration. The precipitates were added to a mixture of water (50 ml) and ethyl acetate (50 ml) and adjusted to pH 6.5 with 5% aqueous sodium bicarbonate. The separated aqueous layer was adjusted to pH 2.5 with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated to give 7-[2-carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (0.5 g).
Workup
- filtrationthe precipitates were collected by filtration
- additionThe precipitates were added to a mixture of water (50 ml) and ethyl acetate (50 ml)
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-f6c4ec5f0c0c4faba43ae265b06c3b31
- Source dataset
- uspto-grants-1984_08
- Patent number
- US04464369
Reaction notes
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