Stannous Chloride → HCID 69881179, compound

Participants

Reaction Steps

(2R,3S)-4-Benzyloxy-3-hydroxy-2-(4′-methoxy-biphenyl-4-sulfonylamino)-butyric acid. To a solution of (2R, 3S)-2-azido-4-benzyloxy-3-hydroxy-butyric acid (50 mg) in methanol (1 mL) is added tin (II) chloride (60 mg) and the reaction mixture is stirred at room temperature for 2 hr. The volatiles are removed under vacuum and the residue is dissolved in dioxane-water (1.6 mL, 1:1, v/v). To the mixture is added triethylamine (0.1 mL) and (4′-methoxy[1,1′-biphenyl]-4-yl)sulfonyl chloride (110 mg) and the mixture is stirred at room temperature for 10 hr. The volatiles are removed under vacuum and the residue is treated with methanol (3 mL) and acetic acid (1 mL). The precipitate is filtered off, the filtrate is concentrated and a crude product is purified using RF HPLC to give (2R,3R)-4-benzyloxy-3-hydroxy-2-(4′-methoxy-biphenyl-4-sulfonylamino)-butyric acid as a white, crystalline solid.

Provenance & Evidence