HCID 14770881, compound → 2-(Sulfanylmethyl)pentanedioic acid

Participants

Reaction Conditions

Reaction Steps

S-Benzoyl-2-mercaptomethylglutaric acid (2 g, 7.08 mmol) was added with stirring to 2-methoxyethylamine (20 mL) kept at 0°-5° C. The resulting solution was stirred for 2 hours at 0° C. and at 30° C. for 1 hour. The thick viscous liquid was evaporated at 60° C. under vacuum to a transparent gel. The residue was dissolved in oxygen-free water (40 mL) and extracted with three portions of EtOAc. The aqueous fraction was acidified with 18% HCl and reextracted with EtOAc. The EtOAc layer was dried over Na2SO4 and evaporated to a thick gel. The residue was dissolved in a mixture of EtOAc/hexane and cooled to -18° C. overnight. The white precipitate formed was collected by filtration, washed and dried under vacuum at room temperature to yield, 1.16 g (91.8%) of the captioned product (mp 75° C.).

Provenance & Evidence