Water → HCID 67797455, compound

HRID 1657252Notes

Reaction equation

HRID 1657252 reaction equation
O.[C:2]([S:6]([CH2:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Ca+2].[OH-]>CS(C)=O>[C:2]([S:6]([CH2:8][C@@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:5])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6093208Calcium HydroxideHCID 14158063HCID 14158063, compound

Product 1

HCID 67797455HCID 67797455, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

550 ml of water are placed in a sulphonation flask having a mechanical stirrer, pH control as well as a dropping funnel and treated while stirring vigorously with 4.85 g (16.36 mmol) of ethyl (RS)-α-[[(RS)-t-butylsulphinyl]methyl]hydrocinnamate (see EPA 0 236 734) in 15 ml of dimethyl sulphoxide. The reaction solution is thereafter adjusted to pH 7.5, treated with 200 mg of α-chymotrypsin and the pH is held constant with 0.037N calcium hydroxide solution. After 220 ml of this calcium hydroxide solution have been consumed (about 45 hours) the unreacted ester is extracted with ethyl acetate, the aqueous phase is adjusted to pH 2 with 30% sulphuric acid and extracted with ethyl acetate. The extracts are washed in succession with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated, whereby there are obtained 2.50 g of (S)-α-[[(RS)-t-butylsulphinyl]methyl]hydrocinnamic acid, MS: 269 (M+H)+.

Workup

  1. additionpH control as well as a dropping funnel and treated
  2. additiontreated with 200 mg of α-chymotrypsin
  3. customAfter 220 ml of this calcium hydroxide solution have been consumed (about 45 hours) the unreacted ester
  4. extractionis extracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extracts are washed in succession with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-71ee02aca6684208b78298e8adb06b65
Source dataset
uspto-grants-1993_10
Patent number
US05256645

Reaction notes

Loading…