Sodium Hydroxide → (2S)-3-[(6-chloro-2-naphthyl)thio]-2-hydroxypropionic acid

HRID 493722Notes

Reaction equation

HRID 493722 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]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66852836Methyl(2S)-3-[(6-chloro-2-naphthyl)thio]-2-hydroxypropionate

Product 1

HCID 59347376(2S)-3-[(6-chloro-2-naphthyl)thio]-2-hydroxypropionic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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.

Workup

  1. additionthe mixture was mixed at room temperature for 3 hours
  2. distillationEthanol was distilled off under reduced pressure
  3. filtrationthe precipitates were collected by filtration
  4. filtrationthe precipitates were then collected by filtration

Sources & evidence

ORD record
ord-8d7f8de58bb64cda8e76018a19d65c79
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

Loading…