Sodium Hydroxide → (2S)-3-[(6-chloro-2-naphthyl)thio]-2-hydroxypropionic acid
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12][CH2:13][C@@H:14]([OH:19])[C:15]([O:17]C)=[O:16])[CH:6]=[CH:5]2.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12][CH2:13][C@@H:14]([OH:19])[C:15]([OH:17])=[O:16])[CH:6]=[CH:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of methyl (2S)-3-[(6-chloronaphthalen-2-yl)thio]-2-hydroxypropionate (5.4 g) obtained in Example 112a) in ethanol (150 mL), a 8 N aqueous sodium hydroxide solution (6.8 mL) was added, and the mixture was mixed at room temperature for 3 hours. Ethanol was distilled off under reduced pressure, and then the precipitates were collected by filtration. The solid was suspended in water (100 mL), pH was adjusted to about 3 with 1 N hydrochloric acid, and the precipitates were then collected by filtration to give the title compound (5.0 g, 97%) as a white solid.