HCID 57857017, compound → HCID 57857025, compound

HRID 561749Notes

Reaction equation

HRID 561749 reaction equation
[S:1]1[C:5]([C@H:6]([OH:31])/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[CH2:14])[CH2:12][C@H:11]([O:15]C3CCCCO3)[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:32]=[CH:33][CH:34]=[CH:35][C:2]1=2>C(O)(=O)C.O.C1COCC1>[S:1]1[C:5]([C@H:6]([OH:31])/[CH:7]=[CH:8]/[C@H:9]2[C:13](=[CH2:14])[CH2:12][C@H:11]([OH:15])[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:32]=[CH:33][CH:34]=[CH:35][C:2]1=2

Participants

3

Reactant 1

HCID 57857017HCID 57857017, compound

Product 1

HCID 57857025HCID 57857025, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Procedure

(Z)-7-((1R,2R,5S)-2-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-hydroxyprop-1-enyl)-3-methylene-5-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid, prepared in Step L, is dissolved in a (4:2:1) solution of acetic acid-water-THF (0.5 M). The solution is stirred for several days at room temperature until the reaction is complete, as judged by TLC. The crude product is purified by flash chromatography on regular silica gel using ethyl acetate-hexane-acetic acid as eluent to afford the title compound 21a.

Workup

  1. customThe crude product is purified by flash chromatography on regular silica gel

Sources & evidence

ORD record
ord-25a05d7bcc3e4ff1bec7b888b3e36668
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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