m-Chloroperbenzoic acid → HCID 131712127, compound

HRID 127646Notes

Reaction equation

HRID 127646 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[C:12]1([CH:18]([O:25][C:26]([C:28]2[N:33]3[C:34](=[O:46])[C@@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C@H:32]3[S:31][CH2:30][C:29]=2[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[S:27])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C1(C(OC([C@@H]2N3C(=O)[C@@H](NC(=O)CC4C=CC=CC=4)[C@H]3SC=C2C2C=CC=CC=2)=S)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[C:12]1([CH:18]([O:25][C:26]([C:28]2[N:33]3[C:34](=[O:46])[C@@H:35]([NH:36][C:37](=[O:45])[CH2:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[C@H:32]3[S:31](=[O:9])[CH2:30][C:29]=2[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)=[S:27])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 131712126HCID 131712126, compoundHCID 131712128HCID 131712128, compound

Product 1

HCID 131712127HCID 131712127, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 410 mg (2.03 mmols) of m-chloroperbenzoic acid in 10 ml of methylene chloride is added to a solution of 1.10 g (1.85 mmols) of a mixture of isomers consisting of 7β-phenylacetylamino-3-phenylthio-3-cephem-4-carboxylic acid diphenylmethyl ester and 7β-phenylacetylamino-3-phenylthio-2-cephem-4α-carboxylic acid diphenylmethyl ester in 11 ml of methylene chloride at 0° C. and the mixture is stirred in an ice bath for 30 minutes. The reaction mixture is diluted with ethyl acetate and washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution and the organic phase is dried over sodium sulphate and evaporated in vacuo. The residue is chromatographed on silica gel thick layer plates with toluene/ethyl acetate, 1:1. 7β-Phenylacetylamino-3-phenylthio-3-cephem-4-carboxylic acid diphenylmethyl ester 1-oxide of Rf value ~0.38 (silica gel; toluene/ethyl acetate, 1:1) is obtained and after recrystallisation from methylene chloride/diethyl ether melts at 180° C. with decomposition.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialthe organic phase is dried over sodium sulphate
  3. customevaporated in vacuo
  4. customThe residue is chromatographed on silica gel thick layer plates with toluene/ethyl acetate, 1:1

Sources & evidence

ORD record
ord-aa5c6506ad1647c7b22aec2dd585c4fd
Source dataset
uspto-grants-1981_03
Patent number
US04256739

Reaction notes

Loading…