Hydrochloric Acid → 2-Benzyl-3-(tert-butylsulfonyl)propanoic acid

HRID 478032Notes

Reaction equation

HRID 478032 reaction equation
C([O:3][C:4](=[O:21])[CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][S:7]([C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:9])=[O:8])C.O.[OH-].[K+].Cl>C1COCC1>[CH2:14]([CH:5]([CH2:6][S:7]([C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:9])=[O:8])[C:4]([OH:21])=[O:3])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 14158057ethyl (RS)-alpha-[(tert-butylsulfonyl)methyl]hydrocinnamate

Product 1

HCID 141580582-Benzyl-3-(tert-butylsulfonyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

550 mg of 2-benzyl-3-tert.-butylsulphonyl-propionic acid ethyl ester are dissolved in 8 ml of THF and then reacted with 5 ml of water and 0.88 ml of 2N potassium hydroxide solution. The mixture is stirred overnight at room temperature, neutralised with 0.88 ml of 2N hydrochloric acid and concentrated by evaporation. The residue is purified by flash chromatography on 30 g of silica gel 60 (eluant H). Yellow oil; m/e 284; 1H-NMR (DMSO-d6): 1.27 ppm (s, 9H); 2.73-3.1 (m, 4H); 3.2-3.5 (m, 1H); 7.2-7.4 (m, 5H); 12.5 (s, 1H).

Workup

  1. concentrationconcentrated by evaporation
  2. customThe residue is purified by flash chromatography on 30 g of silica gel 60 (eluant H)

Sources & evidence

ORD record
ord-24ce2ba82e984f12926ae1ea2361f496
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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