m-Chloroperbenzoic acid → HCID 178448444, compound

HRID 742878Notes

Reaction equation

HRID 742878 reaction equation
[N:1]#[N:2].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:19]([NH:21][C@@H:22]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@H:23]([OH:38])[CH2:24][C@@:25]1([C:34]([NH2:36]=[O:37])=[O:35])[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:20])[CH2:15][S:16]([CH3:18])=[O:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.ClC1C=CC=C(C(OO)=[O:54])C=1>CO>[N:1]#[N:2].[OH2:10].[CH2:3]([O:10][C:11]([NH:13][C@H:14]([C:19]([NH:21][C@@H:22]([CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C@H:23]([OH:38])[CH2:24][C@@:25]1([C:34]([NH2:36]=[O:37])=[O:35])[CH2:29][CH2:28][CH2:27][N:26]1[C:30]([CH3:33])([CH3:32])[CH3:31])=[O:20])[CH2:15][S:16]([CH3:18])(=[O:54])=[O:17])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178504641HCID 178504641, compound

Product 1

HCID 178448444HCID 178448444, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 154 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphinyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide (two diastereomers) in 5 ml of methanol was treated with 84 mg of 3-chloroperbenzoic acid and the solution was stirred at 20° C. for 16 hours. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and 2M sodium hydroxide solution. The organic phase was evaporated and the residue was crystallized from ethyl acetate/n-hexane to give 28 mg of N2 -[3(S)-[[N-(benzyloxycarbonyl)-3-(methylsulphonyl)-L-alanyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide N2 -oxide monohydrate; MS: m/e 633 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between dichloromethane and 2M sodium hydroxide solution
  3. customThe organic phase was evaporated
  4. customthe residue was crystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-a74506e6fff747189d24bebb73920f42
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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