Water → HCID 58303811, compound

Participants

Reaction Conditions

Reaction Steps

To 3.91 g (8.34 mmol) of (+/−)-(2S,3S)-methyl 3-(2-(benzyloxy)-6-nitrophenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate in 45 mL of ethyl acetate was added 11.3 g (5.00 mmol) of tin(II) chloride dihydrate, and the solution was stirred at 22° C. for 3.5 hours. Water, NaHCO3, and ethyl acetate were added, and the mixture was stirred at 22° C. for 1.5 hours. The stirring was stopped, and the mixture left to stand for 16 hours. The organic layer was partially separated from the aqueous layer, and the remaining mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to give (+/−)-(2S,3S)-methyl 3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate, which was used directly in the next step without purification.

Provenance & Evidence