Trifluoroacetic acid → HCID 178429633, compound

HRID 1262770Notes

Reaction equation

HRID 1262770 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:48]1[N:49]=[CH:50][S:51][CH:52]=1)[C:19]([NH:21][CH:22]1[C:46](=[O:47])[N:24]2[C:25]([C:30]([O:32]C(C3C=CC=CC=3)C3C=CC=CC=3)=[S:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]12)=[O:20])=[O:14])(C)(C)C.C(OC(C)C)(C)C.CCCCCC>ClCCl.C1(OC)C=CC=CC=1>[C:13]([CH2:15][O:16][N:17]=[C:18]([C:48]1[N:49]=[CH:50][S:51][CH:52]=1)[C:19]([NH:21][CH:22]1[C:46](=[O:47])[N:24]2[C:25]([C:30]([OH:32])=[S:31])=[C:26]([CH3:29])[CH2:27][S:28][C@H:23]12)=[O:20])([OH:14])=[O:12]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 8058HexaneHCID 131713551HCID 131713551, compound

Product 1

HCID 178429633HCID 178429633, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

Trifluoroacetic acid (14 ml) was added to a stirred suspension of benzhydryl 7-[2-(t-butoxycarbonylmethoxyimino)-2-(4-thiazolyl)acetamido]-3-methylthio-3-cephem-4-carboxylate (syn isomer) (3.5 g) in dichloromethane (7 ml) and anisole (3.5 ml) at ambient temperature and the mixture was stirred for 1.5 hours at the same temperature. To the resulting solution was added isopropyl ether (50 ml) and n-hexane (30 ml) and stirred. The precipitates were collected by filtration, washed with solution of isopropyl ether and n-hexane (1:1). The precipitates were added to a mixture of ethyl acetate and water and adjusted to pH 7.0 with saturated aqueous 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 aqueous layer was adjusted to pH 1.8 with 10% hydrochloric acid under ice cooling. The precipitates were filtered off, washed with cold water and dried over phosphorus pentoxide in vacuo to give 7-[2-(carboxymethoxyimino)-2-(4-thiazolyl)acetamido] -3-methylthio-3-cephem-4-carboxylic acid (syn isomer) (1.03 g).

Workup

  1. stirringstirred
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with solution of isopropyl 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. filtrationThe precipitates were filtered off
  7. washwashed with cold water
  8. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-b1bd044892b94071b5003b9a8f6af58d
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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