HCID 57857014, compound → HCID 57857000, compound

HRID 561735Notes

Reaction equation

[F:1][C:2]([F:35])([CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:3][CH2:4][C@H:5]1[C@H:9]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH2:8][C@H:7]([OH:17])[C@@H:6]1[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[F:35][C:2]([F:1])([CH2:27][O:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:3][CH2:4][C@H:5]1[C@H:9]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH2:8][C:7](=[O:17])[C@@H:6]1[CH2:18]/[CH:19]=[CH:20]\[CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

(Z)-7-((1R,2R,3R,5S)-2-(3,3-Difluoro-4-phenoxybutyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (limiting reagent, prepared in Step G) is dissolved in DCM (0.05 M) and cooled to 0° C. PCC (2 molar equivalents) is added and the reaction mixture is allowed to warm to room temperature with stirring. Upon completion by as indicated 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 intermediate.

Workup

temperatureto warm to room temperature
customthe crude product is purified by flash chromatography on regular silica gel

Sources & evidence

ORD record: ord-de98abc95abc457bb3a4b14c9dcbaddd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063240B2

Reaction notes

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