m-Chloroperbenzoic acid → 1-{4'-[3-Methyl-4-(3-phenethyl-oxiranyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

HRID 1183270Notes

Reaction equation

HRID 1183270 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]=[CH:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:42]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH:27]4[CH:28]([CH2:29][CH2:30][C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[O:42]4)=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 665782161-{4'-[3-Methyl-4-(4-phenyl-but-1-enyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 866523991-{4'-[3-Methyl-4-(3-phenethyl-oxiranyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{4′-[3-methyl-4-(4-phenyl-but-1-enyl)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.343 g, 0.72 mmol) in CH2Cl2 (3.5 mL) was added meta-chloroperoxybenzoic acid (0.181 g, 0.79 mmol), and the reaction was stirred at room temperature overnight. Analytical LCMS indicated the starting material was still present, so additional meta-chloroperoxybenzoic acid was added, and the reaction was stirred overnight at room temperature. After aqueous workup, the organic layer was dried over MgSO4, filtered, and concentrated, and the crude material was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred overnight at room temperature
  2. dry with materialAfter aqueous workup, the organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6261c1b5f46043e7872ef4eac3597cd9
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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