m-Chloroperbenzoic acid → HCID 68133873, compound

HRID 1580508Notes

Reaction equation

HRID 1580508 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:31])=[C:6]([CH:30]=1)[CH2:7][C:8]1[CH:13]([C:14]([OH:16])=[O:15])[N:12]2[C:17](=[O:29])[C@@H:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@H:11]2[S:10][CH:9]=1.ClC1C=CC=C(C(OO)=[O:40])C=1>C(O)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:31])=[C:6]([CH:30]=1)[CH2:7][C:8]1[CH2:9][S:10](=[O:40])[C@@H:11]2[CH:18]([NH:19][C:20](=[O:28])[CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:17](=[O:29])[N:12]2[C:13]=1[C:14]([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131709950HCID 131709950, compound

Product 1

HCID 68133873HCID 68133873, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 2.0 g of 3-(5-fluor-2-hydroxy-benzyl)7β-phenylacetylamino-ceph-2-em-4ξ-carboxylic acid in 10 ml of isopropanol is treated at 0°-5° in small amounts with 1.2 g of 3-chloro-perbenzoic acid and stirred for 2 hours. The reaction mixture is concentrated to half-volume and diluted with 10 ml of diethyl ether. The crystalline precipitate that forms is filtered off and recrystallised from methyl acetate to yield the 3-(5-fluoro-2-hydroxy-benzyl)-7-phenylacetylamino-ceph-3-em-4-carboxylic acid 1-oxide, which melts at 183°-185°; thin-layer chromatogram (silica gel) Rf = 0.48 (system: n-butanol/acetic acid/water 75:7.5:21), Rf = 0.64 (system: n-butanol/ethanol/water 40:10:50) and Rf = 0.77 (system: chloroform/methanol 1:1).

Workup

  1. concentrationThe reaction mixture is concentrated to half-volume
  2. additiondiluted with 10 ml of diethyl ether
  3. filtrationThe crystalline precipitate that forms is filtered off
  4. customrecrystallised from methyl acetate

Sources & evidence

ORD record
ord-b28408c7d8314558b42964196f3dd4f5
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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