Sodium Hydroxide → HCID 57857056, compound

HRID 561770Notes

Reaction equation

[Si:1]([O:8][C@@H:9]([CH:31]1[CH2:39][C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32]1)/[CH:10]=[CH:11]/[C@H:12]1[C@@H:16]([F:17])[CH2:15][C@H:14]([OH:18])[C@@H:13]1[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>CO>[Si:1]([O:8][C@@H:9]([CH:31]1[CH2:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:39]1)/[CH:10]=[CH:11]/[C@H:12]1[C@@H:16]([F:17])[CH2:15][C:14](=[O:18])[C@@H:13]1[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH:28]([CH3:29])[CH3:30])=[O:26])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture consisting of (Z)-isopropyl 7-((1R,2R,3S,5S)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-3-(2,3-dihydro-1H-inden-2-yl)prop-1-enyl)-3-fluoro-5-hydroxycyclopentyl)hept-5-enoate (prepared in Step K, 0.600 g), methanol (5 mL), and 1 N sodium hydroxide (3 mL) was stirred overnight at 0° C. The reaction mixture was acidified with saturated ammonium chloride, extracted into ethyl acetate, washed with brine, and dried over sodium sulfate, filtered, and the solvents were evaporated under reduced pressure. The crude product was purified on silica gel. Elution with hexanes-ethyl acetate (4:1 with 0.4% acetic acid) afforded the title intermediate (0.58 g, 96%).

Workup

extractionextracted into ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvents were evaporated under reduced pressure
customThe crude product was purified on silica gel
washElution with hexanes-ethyl acetate (4:1 with 0.4% acetic acid)

Sources & evidence

ORD record: ord-6d8709e4956441eabdf34a52ebe451d5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063240B2

Reaction notes

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