Water → HCID 57856995, compound

HRID 561759Notes

Reaction equation

HRID 561759 reaction equation
[S:1]1[C:5]([C@H:6]([O:25][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:7][CH2:8][C@H:9]2[C@H:13]([OH:14])[CH2:12][C:11](=[O:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[S:1]1[C:5]([C@H:6]([OH:25])[CH2:7][CH2:8][C@H:9]2[C@H:13]([OH:14])[CH2:12][C:11](=[O:15])[C@@H:10]2[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:4][C:3]2[CH:43]=[CH:44][CH:45]=[CH:46][C:2]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 57857060HCID 57857060, compound

Product 1

HCID 57856995HCID 57856995, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(Z)-7-((1R,2R,3R)-2-((R)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)propyl)-3-hydroxy-5-oxocyclopentyl)hept-5-enoic acid (1 molar equivalent) is dissolved in THF (0.3 M) under a nitrogen atmosphere. A solution consisting of TBAF in THF (1 M, 1.2 molar equivalents) is added and the reaction mixture is stirred at room temperature. Upon completion, as judged by TLC, water is added and most of the THF is removed under reduced pressure. The remaining aqueous solution is extracted with ethyl acetate and is washed with water 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 ethyl acetate-hexanes (+0.4% acetic acid) to afford the title compound.

Workup

  1. additionis added
  2. customis removed under reduced pressure
  3. extractionThe remaining aqueous solution is extracted with ethyl acetate
  4. washis washed with water and brine
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent is evaporated
  8. customThe crude product is purified by flash chromatography on regular silica gel
  9. washeluted with ethyl acetate-hexanes (+0.4% acetic acid)

Sources & evidence

ORD record
ord-904e1736395f4f98b889eda9d5654591
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

Loading…