Hydrochloric Acid → (2S)-3-[(6-chloro-2-naphthyl)thio]-2-hydroxypropionic acid

HRID 2366526Notes

Reaction equation

HRID 2366526 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14][CH2:15][C@@H:16]([OH:21])[C:17]([O:19]C)=[O:18])[CH:8]=[CH:7]2.Cl>C(O)C.O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([S:14][CH2:15][C@@H:16]([OH:21])[C:17]([OH:19])=[O:18])[CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

An aqueous 8N sodium hydroxide solution (6.8 mL) was added to a suspension of methyl (2S)-3-[(6-chloronaphthalen-2-yl)thio]-2-hydroxypropionate (5.4 g) obtained in Reference Example 1a) in ethanol (150 mL) and the mixture was stirred at room temperature for 3 hours. Ethanol was distilled off under reduced pressure and then the resulting precipitate was obtained by filtration. The solid was suspended in water (100 mL), pH of the suspension was adjusted to about 3 with 1N hydrochloric acid and then the precipitate was collected by filtration to obtain the title compound (5.0 g, 97%) as a white solid.

Workup

  1. distillationEthanol was distilled off under reduced pressure
  2. customthe resulting precipitate was obtained by filtration
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-9cd02a63990d4536a1f3051ab61c43b3
Source dataset
uspto-grants-2014_04
Patent number
US08697865B2

Reaction notes

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