2-Chloromandelic acid → (S(R*,R*))-2-amino-1-phenylpropane-1,3-diol

Participants

Reaction Steps

(The compound of the general formula (II)—wherein R1 is a hydroxy-methyl group, R2 is a phenyl group, R3 is a hydroxy group) Racemic 2-hydroxy-2-(2-chlorophenyl)acetic acid (20.0 g 107 mmol) was dissolved in 60 cm3 of ethylacetate saturated with water and (1S, 2S)-(+)-1-phenyl-2-amino-1,3-propane-diol (18.0 g 107.5 mmol) was added thereto and then the mixture was seed by a salt formed from (S)-(+)-2-hydroxy-2-(2-chlorophenyl)acetate and (1S, 2S)-(+)-1-phenyl 2-amino-1,3-propane-diol at room temperature.

Provenance & Evidence