m-Chloroperbenzoic acid → HCID 15550201, compound

HRID 379317Notes

Reaction equation

HRID 379317 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C@H:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=4)[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:46])C=1>ClCCl.CCOC(C)=O>[C:1]1([C:7]2[N:8]=[C:9]([C:18]34[O:46][CH:23]3[CH2:22][CH2:21][CH2:20][C@H:19]4[CH2:24][C:25]3[CH:26]=[C:27]([CH:35]=[CH:36][CH:37]=3)[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 15550200HCID 15550200, compound

Product 1

HCID 15550201HCID 15550201, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl (S)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenoxy}acetate (800 mg) and m-chloroperbenzoic acid (600 mg) in dichloromethane (20 ml) was stirred for 2 hours at room temperature. The mixture was diluted with EtOAc and washed with water and brine. Then, it was dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to give ethyl {3-{[(1S)-2-(4,5-diphenyloxazol-2-yl) -2,3-epoxy-1-cyclohexyl]methyl}phenoxy}-acetate (400 mg).

Workup

  1. washwashed with water and brine
  2. dry with materialThen, it was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-780bd0b5852c4d5ca22b78e77b9ecb04
Source dataset
uspto-grants-2001_10
Patent number
US06297267B1

Reaction notes

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