m-Chloroperbenzoic acid → N-[2-(1-oxiranylethoxy)phenyl]acetamide

HRID 496222Notes

Reaction equation

HRID 496222 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:15])[CH3:14])[CH:3]=[CH2:4].ClC1C=CC=C(C(OO)=[O:24])C=1>>[O:24]1[CH2:4][CH:3]1[CH:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH:12][C:13](=[O:15])[CH3:14])[CH3:1]

Participants

3

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22313621N-{2-[(1-Methyl-2-propenyl)oxy]phenyl}acetamide

Product 1

HCID 22313695N-[2-(1-oxiranylethoxy)phenyl]acetamide

Procedure

The compound was prepared from N-{2-[(1-Methyl-2-propenyl)oxy]phenyl}acetamide (549 mg, 2.67 mmol) and m-chloroperbenzoic acid (80%, 923 mg, 4.28 mmol) analogously to that described in Example 8 (ii). Purification was done on silica gel with petroleum ether/ethyl acetate 10/15 as eluent. This gave separation of the two diastereomeric pairs.

Workup

  1. customPurification
  2. customThis gave separation of the two diastereomeric pairs

Sources & evidence

ORD record
ord-535d780db0824b15b9db35f3da1cea08
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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