HCID 67000377, compound → HCID 57857063, compound

HRID 561740Notes

Reaction equation

HRID 561740 reaction equation
C([O:9][C@@H:10]1[CH2:18][C@@H:13]2[O:14][C:15](=[O:17])[CH2:16][C@@H:12]2[C@H:11]1/[CH:19]=[CH:20]/[C@H:21]([C:40]1[S:44][C:43]2[CH:45]=[CH:46][CH:47]=[CH:48][C:42]=2[CH:41]=1)[O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)C1C=CC=CC=1>CO.C(=O)([O-])[O-].[K+].[K+]>[S:44]1[C:40]([C@H:21]([O:22][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)/[CH:20]=[CH:19]/[C@@H:11]2[C@@H:12]3[C@@H:13]([O:14][C:15](=[O:17])[CH2:16]3)[CH2:18][C@H:10]2[OH:9])=[CH:41][C:42]2[CH:48]=[CH:47][CH:46]=[CH:45][C:43]1=2

Participants

4

Reactant 1

HCID 67000377HCID 67000377, compound

Product 1

HCID 57857063HCID 57857063, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture consisting of (3aR,4R,5R,6aS)-4-((R,E)-3-(benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (6a, limiting reagent) in methanol (0.2 M) and potassium carbonate (0.6 molar equivalent) is stirred at room temperature and the reaction progress is monitored by TLC every 30 minutes. After complete consumption of starting material, the reaction mixture is acidified with 5% aqueous KHSO4 and diluted with brine. The product is extracted with ethyl acetate twice. The combined organic layers are dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate (1:1) to afford the title intermediate 7a.

Workup

  1. customAfter complete consumption of starting material
  2. additiondiluted with brine
  3. extractionThe product is extracted with ethyl acetate twice
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product is purified by flash chromatography on regular silica gel
  8. washeluted with hexanes-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-4f8772d476604e5cb025987b0ee691d6
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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