Hydrochloric Acid → HCID 86744465, compound

HRID 703280

Reaction equation

HRID 703280 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 86744465HCID 86744465, compoundYield 93%

Procedure

To 10.65 g (42.43 mmole) of methyl (2S, 3R)-2-(N-benzoylamino)methyl-3-hydroxybutanoate was added 70 ml of a 10% hydrochloric acid aqueous solution at room temperature to form a solution. The solution was heated at reflux for 4.5 hours and then allowed to cool to room temperature. The precipitated benzoic acid was separated by filtration, and the filtrate was washed twice with 100 ml portions of toluene. The aqueous layer was concentrated under reduced pressure to obtain 6.67 g (yield: 93%) of (2S, 3R)-2-aminomethyl-3-hydroxybutanoic acid hydrochloride.

Workup

  1. customto form a solution
  2. temperatureThe solution was heated
  3. temperatureat reflux for 4.5 hours
  4. customThe precipitated benzoic acid was separated by filtration
  5. washthe filtrate was washed twice with 100 ml portions of toluene
  6. concentrationThe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b82bab42b2c1419abdb6c1462a26f5ac
Source dataset
uspto-grants-1991_01
Patent number
US04981992

Linked notes

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