Triethylamine → (S)-2-Methyl-3-(3-methyl-5-vinyl-phenylmethanesulfonyl)-propionic acid

HRID 1432104Notes

Reaction equation

HRID 1432104 reaction equation
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].C(N(CC)CC)C.Br[C:16]1[CH:17]=[C:18]([CH2:23][S:24]([CH2:27][C@@H:28]([CH3:32])[C:29]([OH:31])=[O:30])(=[O:26])=[O:25])[CH:19]=[C:20]([CH3:22])[CH:21]=1>C(O)CC.CCOC(C)=O>[CH3:32][C@H:28]([CH2:27][S:24]([CH2:23][C:18]1[CH:19]=[C:20]([CH:21]=[CH2:16])[CH:22]=[C:1]([CH3:2])[CH:17]=1)(=[O:25])=[O:26])[C:29]([OH:31])=[O:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 68544363(S)-3-(3-bromo-5-methyl-phenylmethanesulfonyl)-2-methyl-propionic acid

Product 1

HCID 68541338(S)-2-Methyl-3-(3-methyl-5-vinyl-phenylmethanesulfonyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium vinyltrifluoroborate (247 mg, 1.8 mmol), triethylamine (0.21 ml, 1.5 mmol) and [1,1′-bis(diphenylphosphino-κP)ferrocene]dichloro-palladium (24 mg) are added to (S)-3-(3-bromo-5-methyl-phenylmethanesulfonyl)-2-methyl-propionic acid (0.5 g, 1.5 mmol) in 25 ml propanol. The mixture is stirred under argon for 2.5 hrs at reflux. After cooling to rt the mixture is diluted with EtOAc, washed with 0.5 N aqueous hydrochloric acid and brine, dried over magnesium sulfate, and the solvents are evaporated. The residue is purified by chromatography on silica gel (flashmaster, DCM to DCM/methanol 9/1) followed by crystallization from DCM/diethyl ether/hexane to give the title compound as off-white crystals.

Workup

  1. temperatureat reflux
  2. washwashed with 0.5 N aqueous hydrochloric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvents are evaporated
  5. customThe residue is purified by chromatography on silica gel (flashmaster, DCM to DCM/methanol 9/1)
  6. customfollowed by crystallization from DCM/diethyl ether/hexane

Sources & evidence

ORD record
ord-264b5b54b65b45ef9759429cfbba757d
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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