Chloroacetyl chloride → (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 a solution of 150 ml of dichloromethane containing 5.00 g of L-thioprolineamide hydrochloride thus obtained 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 was added a dichloromethane solution containing 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 anhydrous magnesium sulfate, filtered and concentrated under reduced pressure, and subsequently, the residue was crystallized from ether to obtain 4.82 g of (R)-3-chloroacetyl-4-cyanothiazolidine as yellow-brownish crystals.

1. customthus obtained
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 anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customsubsequently, the residue was crystallized from ether

ORD record

ord-f08c858388c845b3b49e0f53cf62d5d6

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07160877B2