Tetrahydrofuran → HCID 178459663, compound

Participants

Reaction Steps

To a solution of allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (539 mg, 1.30 mmol) in ethanol(40 ml)/THF(3 ml) was added p-toluenesulfonic acid monohydrate (50 ml). Four hours later the solvent was removed in vacuo. The residue was made alkaline by adding an aqueous 1N NaOH solution. To the mixture were added ethyl acetate and hexane, and the mixture was separated with a separating funnel. To the aqueous layer was added 6N hydrochloric acid, and the mixture was separated with a separating funnel. The aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution, was dried over magnesium sulfate and the organic solvent was removed under reduced pressure to give allyl (2S)-2-(hydroxymethyl)-4-(2-mercapto-1,3-thiazol-4-yl)-3,6-dihydro-1(2 H)-pyridinecarboxylate (218 mg, 55%).

Provenance & Evidence