HCID 57857071, compound → HCID 57857010, compound

HRID 561747Notes

Reaction equation

HRID 561747 reaction equation
[S:1]1[C:5]([C@H:6]([O:32][Si:33]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[CH2:14])[CH2:12][C@H:11]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29])=[CH:4][C:3]2[CH:50]=[CH:51][CH:52]=[CH:53][C:2]1=2>CO.[Li+].[OH-].C(OCC)(=O)C>[S:1]1[C:5]([C@H:6]([O:32][Si:33]([C:46]([CH3:48])([CH3:49])[CH3:47])([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[CH2:14])[CH2:12][C@H:11]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:4][C:3]2[CH:50]=[CH:51][CH:52]=[CH:53][C:2]1=2

Participants

5

Reactant 1

HCID 57857071HCID 57857071, compound

Product 1

HCID 57857010HCID 57857010, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
4 °C

Procedure

(Z)-Methyl 7-((1R,2R,5S)-2-((R,E)-3-(benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-3-methylene-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoate (17a, limiting reagent) is dissolved in a 3:1 methanol and 1 N LiOH solution (0.01 M) and stirred at 4° C. Upon completion of the reaction, as judged by TLC, the reaction mixture is diluted with ethyl acetate, washed with 5% aqueous KHSO4 and brine. The organic phase is dried over sodium sulfate, filtered, and the solvent is evaporated. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate to afford the title intermediate 19a.

Workup

  1. customUpon completion of the reaction
  2. washwashed with 5% aqueous KHSO4 and brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customThe crude product is purified by flash chromatography on regular silica gel
  7. washeluted with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-d7575f31de264ad0913dda2efcb14f02
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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