Selenium Dioxide → HCID 15550209, compound

HRID 379316Notes

Reaction equation

HRID 379316 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.[Se](=O)=[O:39]>ClCCl>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[C: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])([OH:39])[CH2:20][CH2:21][CH2:22][CH:23]=3)[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.[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][CH:22]([OH:39])[CH:23]=3)[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 24007Selenium DioxideHCID 15550200HCID 15550200, compound

Product 2

HCID 15550209HCID 15550209, compoundHCID 86757469HCID 86757469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl (S)-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenoxy}acetate (380 mg) (prepared by a method described in WO 95/17393) and selenium dioxide (SeO2) (170 mg) in dichloromethane (230 ml) was refluxed for 2 hours under stirring. The mixture was filtered and the filtrate was evaporated. The residue was purified by chromatography on silica gel to give ethyl {3-{[2-(4,5-diphenyloxazole-2-yl)-1-hydroxy-2-cyclohexen-1-yl]-methyl}phenoxy}acetate (60 mg) as a first fraction and ethyl {3-{[(1S)-2-(4,5-diphenyloxazol-2-yl)-4-hydroxy-2-cyclohexen-1-yl]methyl}phenoxy}acetate (80 mg) as a second fraction.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-67344bc6f61140eeb678dc4658521ab2
Source dataset
uspto-grants-2001_10
Patent number
US06297267B1

Reaction notes

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