m-Chloroperbenzoic acid → HCID 86746254, compound

HRID 54091Notes

Reaction equation

[N:1]#[N:2].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:18]([NH:20][C@@H:21]([CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:22]([OH:36])[CH2:23][C@@:24]1([C:33]([NH2:35])=[O:34])[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:19])[CH2:15][S:16][CH3:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClC1C=CC=C(C(OO)=[O:52])C=1>CO>[N:1]#[N:2].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:18]([NH:20][C@@H:21]([CH2:37][C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C@H:22]([OH:36])[CH2:23][C@@:24]1([C:33]([NH2:35])=[O:34])[CH2:28][CH2:27][CH2:26][N:25]1[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:19])[CH2:15][S:16]([CH3:17])=[O:52])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 193 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-S-methyl-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide in 2 ml of methanol was cooled to -70° C. A solution of 62 mg of 3-chloroperbenzoic acid in 5 ml of methanol was added and the mixture was stirred at -70° C. for 30 minutes. The solvent was then removed by evaporation and the residue was chromatographed on silica gel using System G for the elution to give 62 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphinyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide as a 1:1 mixture of diastereomers; MS: m/e 601 [M+H]+.

Workup

customThe solvent was then removed by evaporation
customthe residue was chromatographed on silica gel using System G for the elution

Sources & evidence

ORD record: ord-883c57b2d95c4ea9bf1ce449302bc204
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620987

Reaction notes

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