Hydrochloric Acid → (2S,3R)-2-aminomethyl-3-hydroxybutyric acid hydrochloride

HRID 1090290Notes

Reaction equation

HRID 1090290 reaction equation
C([NH:9][CH2:10][C@@H:11]([C@H:16]([OH:18])[CH3:17])[C:12]([O:14]C)=[O:13])(=O)C1C=CC=CC=1.[ClH:19]>>[ClH:19].[NH2:9][CH2:10][C@@H:11]([C@H:16]([OH:18])[CH3:17])[C:12]([OH:14])=[O:13]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 10060699(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

Product 1

HCID 86744465(2S,3R)-2-aminomethyl-3-hydroxybutyric acid hydrochlorideYield 93%

Procedure

10.65 g (42.43 mmol) of methyl (2S,3R)-2-(N-bezoylaminomethy)-3-hydroxybutyrate was added to the 70 ml of 10% aqueous HCl solution at room temperature. The mixture was refluxed for 4.5 hours, then cooled to room temperature. Precipitated benzoic acid was filtered out, the filtrate was washed twice with 100 ml toluene, and the aqueous layer was taken and concentrated under reduced pressure to obtain 6.67 g of the title compound (yield: 93%).

Workup

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. filtrationPrecipitated benzoic acid was filtered out
  3. washthe filtrate was washed twice with 100 ml toluene
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a967d38bde5b4c1787141251d0b8b1b8
Source dataset
uspto-grants-1992_01
Patent number
US05081239

Reaction notes

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