Calcium Chloride → 2-Benzyl-3-(tert-butylsulfonyl)propanoic acid

Temperature

38 °C

1.60 g (5.12 mmol) of ethyl (RS)-α-[(tert-butylsulfonyl)methyl]hydrocinnamate were treated with 50 ml of aqueous 5 mM calcium chloride solution and the reaction mixture was warmed to 38° C. while stirring. The pH value was adjusted to 7.5 with 1N sodium hydroxide solution. The hydrolysis was started by the addition of 150 mg of Savinase 6.0 T (NOVO, 2880 Bagsvaerd, Denmark). The pH value was held constant at 7.5 using automatic titration by dosing-in 1N sodium hydroxide solution while stirring vigorously at 38° C. After a consumption of 2.39 ml of 1N sodium hydroxide solution (after 21.3 hours), the reaction mixture was washed twice with 50 ml of ethyl acetate. The aqueous phase was acidified to pH 2.2 with 25% hydrochloric acid and extracted twice with 50 ml of ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated at 1200 Pa/40° C., whereby there were obtained 690 mg (2.42 mmol, 47%, 94% of theory) of (S)-α-[(tert-butylsulfonyl)methylhydrocinnamic acid in the form of white crystals, which had an enantomeric excess of >99%. In order to determine the purity by gas chromatography, the compound obtained was silylated and likewise had a purity of >99%.

1. additionThe hydrolysis was started by the addition of 150 mg of Savinase 6.0 T (NOVO, 2880 Bagsvaerd, Denmark)
2. stirringwhile stirring vigorously at 38° C
3. customAfter a consumption of 2.39 ml of 1N sodium hydroxide solution (after 21.3 hours)
4. washthe reaction mixture was washed twice with 50 ml of ethyl acetate
5. extractionextracted twice with 50 ml of ethyl acetate
6. dry with materialThe organic phase was dried over magnesium sulfate
7. customevaporated at 1200 Pa/40° C.

ORD record

ord-ce75736edb5347c3b54d9f672cfc0b49

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05223432