m-Chloroperbenzoic acid → HCID 131713534, compound

HRID 1262756Notes

Reaction equation

HRID 1262756 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:49][O:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:10]([NH:12][CH:13]2[C:47](=[O:48])[N:15]3[C:16]([C:31]([O:33][CH:34]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:32])=[C:17]([O:20][S:21]([C:24]4[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=4)(=[O:23])=[O:22])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].ClC1C=CC=C(C(OO)=[O:67])C=1>C(Cl)Cl>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:49][O:50][CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C:10]([NH:12][CH:13]2[C:47](=[O:48])[N:15]3[C:16]([C:31]([O:33][CH:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)=[O:32])=[C:17]([O:20][S:21]([C:24]4[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=4)(=[O:22])=[O:23])[CH2:18][S:19](=[O:67])[C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131713533HCID 131713533, compound

Product 1

HCID 131713534HCID 131713534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-tosyloxy-3-cephem-4-carboxylate (syn isomer) (3.2 g) in methylene chloride (20 ml) was added m-chloroperbenzoic acid (1.62 g) at ambient temperature. The mixture was stirred for an hour. The resulting solution was concentrated under reduced pressure and the residue was subjected to column chromatography on silica gel (eluent: benzene-ethyl acetate) to give benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-tosyloxy-3-cephem-4-carboxylate-1-oxide (syn isomer), 0.6 g).

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9ad67aebf4df40d7805ffce2fdf04135
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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