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

HRID 20213Notes

Reaction equation

HRID 20213 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-625a28b6225a4bcfbb87321ae64ad33e
Source dataset
uspto-grants-2010_06
Patent number
US07745623B2

Reaction notes

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