Imidazole → HCID 67000377, compound

HRID 561739Notes

Reaction equation

HRID 561739 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:9])[CH3:8].[C:24]([O:32][C@@H:33]1[CH2:41][C@@H:36]2[O:37][C:38](=[O:40])[CH2:39][C@@H:35]2[C@H:34]1/[CH:42]=[CH:43]/[C@H:44]([C:46]1[S:50][C:49]2[CH:51]=[CH:52][CH:53]=[CH:54][C:48]=2[CH:47]=1)[OH:45])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.C(OCC)(=O)C>[C:24]([O:32][C@@H:33]1[CH2:41][C@@H:36]2[O:37][C:38](=[O:40])[CH2:39][C@@H:35]2[C@H:34]1/[CH:42]=[CH:43]/[C@H:44]([C:46]1[S:50][C:49]2[CH:51]=[CH:52][CH:53]=[CH:54][C:48]=2[CH:47]=1)[O:45][Si:10]([C:7]([CH3:9])([CH3:8])[CH3:6])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 57857007HCID 57857007, compound2×

Product 1

HCID 67000377HCID 67000377, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A stirring mixture consisting of (3aR,4R,5R,6aS)-4-((R,E)-3-(benzo[b]thiophen-2-yl)-3-hydroxyprop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate (5a, limiting reagent) and imidazole (1.1 molar equivalents) in DMF (5 M in 5a) is cooled to 0° C. under a nitrogen atmosphere. A solution consisting of TBDPSCl (1.1 molar equivalents) in DMF is added slowly. Upon completion of the reaction, as judged by TLC, the reaction mixture is diluted with ethyl acetate and is washed with water and brine. The organic layer is 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 to afford the title intermediate 6a.

Workup

  1. additionis added slowly
  2. customUpon completion of the reaction
  3. washis washed with water and brine
  4. dry with materialThe organic layer is 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

Sources & evidence

ORD record
ord-bc53bb0c7c884baaabed3a8810b49035
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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