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

HRID 1590770Notes

Reaction equation

HRID 1590770 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-benzoylamino)-methyl]-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-f606c845941a445886812fd5eb5020c2
Source dataset
uspto-grants-1993_04
Patent number
US05204460

Reaction notes

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