m-Chloroperbenzoic acid → Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate 1-oxide

HRID 1074361Notes

Reaction equation

HRID 1074361 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:37]2[N:38]=[C:39]([NH:42][CH:43]=[O:44])[S:40][CH:41]=2)[C:7]([NH:9][C@@H:10]2[C:35](=[O:36])[N:12]3[C:13]([C:19]([O:21][CH:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[C:14]([CH2:17][Cl:18])[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:53])C=1>C(Cl)Cl>[CH:1]1([O:4][N:5]=[C:6]([C:37]2[N:38]=[C:39]([NH:42][CH:43]=[O:44])[S:40][CH:41]=2)[C:7]([NH:9][C@@H:10]2[C:35](=[O:36])[N:12]3[C:13]([C:19]([O:21][CH:22]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[C:14]([CH2:17][Cl:18])[CH2:15][S:16](=[O:53])[C@H:11]23)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131716070Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 131716071Benzhydryl 7beta-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer) (3 g) in methylene chloride (300 ml) was dropwise added a solution of m-chloroperbenzoic acid (0.79 g, 80% purity) in methylene chloride (10 ml) below 5° C. The mixture was stirred for 1.5 hours below 5° C. to give precipitates. The precipitates were collected, washed with methylene chloride, and dried over phosphorus pentoxide to give benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4carboxylate 1-oxide (syn isomer) as a solid.

Workup

  1. customto give
  2. customprecipitates
  3. customThe precipitates were collected
  4. washwashed with methylene chloride
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-677b2ddaf97d4d70b6560ac4a37c49a0
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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