Dichloromethane → (4R)-3-(chloroacetyl)-1,3-thiazolidine-4-carbonitrile

L-thioprolineamide hydrochloride was synthesized according to the process described in the literature (Ashworth et. al, Bioorg. Med. Chem. Lett., Vol. 6, pp. 2745-2748, 1996). 2.36 ml of chloroacetyl chloride was added to 150 ml of a dichloromethane solution containing 5.00 g of the thus obtained L-thioprolineamide hydrochloride and 8.67 ml of triethylamine under ice-cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture were added 4.8 ml of pyridine and 8.4 ml of trifluoroacetic anhydride, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was washed with an aqueous 10% HCl solution and water, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Subsequently, the residue was crystallized from ether to obtain 4.82 g of (R)-3-chloroacetyl-4-cyanothiazolidine as a yellowish brown crystal.

1. temperaturecooling
2. stirringthe mixture was further stirred at room temperature for 1 hour
3. washThe reaction mixture was washed with an aqueous 10% HCl solution and water
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customSubsequently, the residue was crystallized from ether

ORD record

ord-373a428d2321428a867074777bfe322f

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07666869B2