Trifluoroacetic acid → 7-[2-Carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid

HRID 358086Notes

Reaction equation

HRID 358086 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:39]=[CH:38][S:37][N:36]=1)[C:19]([NH:21][CH:22]1[C:33](=[O:34])[N:24]2[C:25]([C:30]([OH:32])=[O:31])=[C:26]([Cl:29])[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:35]1[N:39]=[CH:38][S:37][N:36]=1)[C:19]([NH:21][CH:22]1[C:33](=[O:34])[N:24]2[C:25]([C:30]([OH:32])=[O:31])=[C:26]([Cl:29])[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 1317136357-[2-Tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid

Product 1

HCID 1317136347-[2-Carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acidYield 69.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (5.2 ml) was added to a suspension of 7-[2-tert-butoxycarbonylmethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer) (1.3 g) in methylene chloride (2.5 ml) and anisole (1.3 ml) at ambient temperature, and the mixture was stirred for 1.5 hours at the same temperature. To the resultant solution was added a mixture of diisopropyl ether (30 ml) and n-hexane (15 ml), followed by stirring. The precipitates were collected by filtration and added to a mixture of ethyl acetate and water, followed by adjusting to pH 7.5 with 20% aqueous sodium carbonate. The separated aqueous layer was adjusted to pH 1.8 with 10% hydrochloric acid and saturated with sodium chloride. The resultant aqueous soluiton was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran (2:1 by volume). The extract was washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and then evaporated to give 7-[2-carboxymethoxyimino-2-(1,2,4-thiadiazol-3-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer) (0.8 g).

Workup

  1. stirringby stirring
  2. filtrationThe precipitates were collected by filtration
  3. additionadded to a mixture of ethyl acetate and water
  4. extractionThe resultant aqueous soluiton was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran (2:1 by volume)
  5. washThe extract was washed with a saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d5571382eb804138a75d8985baaf3077
Source dataset
uspto-grants-1984_08
Patent number
US04464369

Reaction notes

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