Cesium carbonate → HCID 57857026, compound

HRID 561763Notes

Reaction equation

[Si:1]([O:18][CH2:19][C@H:20]1[C@@H:24]([F:25])[CH2:23][C@H:22]([OH:26])[C@@H:21]1[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:43][CH2:44][CH3:45].OS([O-])(=O)=O.[K+]>CN(C=O)C>[Si:1]([O:18][CH2:19][C@H:20]1[C@@H:24]([F:25])[CH2:23][C@H:22]([OH:26])[C@@H:21]1[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH2:31][CH2:32][C:33]([O:35][CH:44]([CH3:45])[CH3:43])=[O:34])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution consisting of (Z)-7-((1R,2S,3S,5S)-2-((tert-butyldiphenylsilyloxy)methyl)-3-fluoro-5-hydroxycyclopentyl)hept-5-enoic acid (prepared in Step C, 30.8 g, 61.6 mmol) in anhydrous DMF (1.2 L) was added cesium carbonate (30.0 g, 92.4 mmol) followed by iodopropane (22 g, 13 mL, 130 mmol). The reaction mixture was heated to 50° C. and stirred for 1.5 hours, monitoring by TLC. The reaction mixture was acidified with 5% KHSO4, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and evaporated. The crude product was purified on silica gel, eluted with hexanes-ethyl acetate (4:1) to afford the title intermediate (28.6 g, 86%).

Workup

extractionextracted with ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe crude product was purified on silica gel
washeluted with hexanes-ethyl acetate (4:1)

Sources & evidence

ORD record: ord-f3866bcd23444107af482943db50c7ed
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063240B2

Reaction notes

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