Acetic Acid → HCID 86747330, compound

HRID 1657057Notes

Reaction equation

HRID 1657057 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[C:16]#[C:17][S:18][CH2:19][C@@H:20]([O:26][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]=1[CH3:44].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[C:9]=2[C:16]#[C:17][S:18][CH2:19][C@@H:20]([OH:26])[CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:4][C:3]=1[CH3:44]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 86747331HCID 86747331, compound

Product 1

HCID 86747330HCID 86747330, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (S)-4-[[[4'-fluoro-3,3',5-trimethyl[1,1'-biphenyl]-2-yl]ethynyl]thio]-3-(t-butyldiphenylsilyloxy)butanoic acid, methyl ester (1.2 g, 1.9 mM) in dry tetrahydrofuran (10 ml) was treated with glacial acetic acid (0.43 ml, 7.70 mM, 4.0 eq) followed by a 1.0M tetrabutylammonium fluoride solution in tetrahydrofuran (5.78 ml, 5.78 mM, 3.0 eq) and the dark reaction mixture stirred overnight at room temperature under argon. The mixture was diluted with 10 ml of ice water and extracted with ethyl acetate (2×). The organic phase was washed with saturated NaHCO3 and brine, then dried over anhydrous Na2SO4 and evaporated to give a dark oily residue. The crude oil was purified by flash chromatography (Merck Silica gel, 20% ethyl acetate/hexane) affording the title compound as a dark oil (0.53 g, 71.6%).

Workup

  1. customthe dark reaction mixture
  2. extractionextracted with ethyl acetate (2×)
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated
  6. customto give a dark oily residue
  7. customThe crude oil was purified by flash chromatography (Merck Silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-75ca7d1fb16241de849c1d18674f9811
Source dataset
uspto-grants-1993_10
Patent number
US05256692

Reaction notes

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