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

HRID 462598Notes

Reaction equation

HRID 462598 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:35]=[CH:36][S:37][CH:38]=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.CCCCCC>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:34]1[N:35]=[CH:36][S:37][CH:38]=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

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 1317142047-[2-t-Butoxycarbonylmethoxyimino2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317142067-[2-Carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acidYield 87.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (5.2 ml) was added to a suspension of 7-[2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.3 g) in methylene chloride (2 ml) and anisole (1.3 ml) at ambient temperature and the mixture was stirred for 1.5 hours at the same temperature. To the resulting solution was added diisopropyl ether (40 ml) and n-hexane (30 ml) under stirring. The precipitates were collected by filtration, washed with solution of diisopropyl ether and n-hexane (1:1). The precipitates were added to a mixture of ethyl acetate and water and the mixture was adjusted to pH 7.5 with saturated aqueous solution of potassium carbonate. The separated aqueous layer was adjusted to pH 4.0 with 10% hydrochloric acid and the solution was washed with ethyl acetate. The resulting solution was adjusted to pH 1.8 with 10% hydrochloric acid under ice-cooling. The precipitates were collected by filtration, washed with cold water and dried over phosphorus pentoxide in vacuo to give 7-[2-carboxymethoxyimino-2-(4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.0 g).

Workup

  1. stirringunder stirring
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with solution of diisopropyl ether and n-hexane (1:1)
  4. additionThe precipitates were added to a mixture of ethyl acetate and water
  5. washthe solution was washed with ethyl acetate
  6. temperaturecooling
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with cold water
  9. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-203a8cbc63df4fbb88dcd00aa7dfd418
Source dataset
uspto-grants-1985_05
Patent number
US04515788

Reaction notes

Loading…