m-Chloroperbenzoic acid → HCID 86746246, compound

HRID 1757739Notes

Reaction equation

HRID 1757739 reaction equation
[OH:1][C@@H:2]([C@@H:16]([NH:24][C:25](=[O:44])[C@H:26]([CH2:40][C:41](=[O:43])[NH2:42])[NH:27][C:28]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1)=[O:29])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:3][NH:4][C:5](=[O:15])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11]([CH3:14])([CH3:13])[CH3:12].ClC1C=CC=C(C(OO)=[O:53])C=1>ClCCl>[C:11]([N:7]1[CH2:8][CH2:9][CH2:10][C@H:6]1[C:5]([NH+:4]([O-:53])[CH2:3][C@@H:2]([OH:1])[C@@H:16]([NH:24][C:25](=[O:44])[C@H:26]([CH2:40][C:41](=[O:43])[NH2:42])[NH:27][C:28]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=1)=[O:29])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 70047404HCID 70047404, compound

Product 1

HCID 86746246HCID 86746246, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.422 g of N -[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]amino]butyl]-N1 -tert.butyl-L-prolinamide and 142 mg of 3-chloroperbenzoic acid in 10 ml of dichloromethane was stirred at 20° C. for 1 hour. The solvent was then removed by evaporation and the residue was chromatographed on silica gel using dichloromethane/methanol (9:1) for theelution to give 289 mg of N1 -tert.butyl-N2 -[2(R)-hydroxy-4-phenyl-3(S)-[[N-(2-quinolylcarbonyl)-L-asparaginyl]amino]-butyl]L-prolinamide N2 -oxide as a white solid; MS: m/e 619 [M+H]+.

Workup

  1. customThe solvent was then removed by evaporation
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-6b484e7e0e234432a7fc5bb755786344
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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