Water → HCID 86654320, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.95 g (6.71 mmol) of (+/−)-(2S,3S)-methyl 3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoate in 34 mL of 9:1 methanol/water was added 5.64 g (67.1 mmol) of sodium bicarbonate. The mixture was refluxed for 16 hours, cooled to 22° C., and 500 mL of water was added. The aqueous layer was washed with ethyl acetate (2×) and then acidified to ph 4-5 with conc. HCl. The mixture was extracted 3 times with a 7:3 ethyl acetate/methanol solution. The organic layers were combined, dried (Na2SO4), and evaporated to give (+/−)-(2S,3S)-3-(2-amino-6-(benzyloxy)phenylthio)-2-hydroxy-3-(4-methoxyphenyl)propanoic acid.

Provenance & Evidence