Methanol → 4-Amino-2(S)-hydroxybutyric acid ethyl ester, hydrochloride

HRID 1587982

Reaction equation

HRID 1587982 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C@H:14]([OH:18])[C:15]([OH:17])=[O:16])=O)C1C=CC=CC=1.S(Cl)([Cl:21])=O.[C:23](OCC)(=O)[CH3:24].CO>C(O)C.[Pd]>[ClH:21].[CH2:23]([O:17][C:15](=[O:16])[C@@H:14]([OH:18])[CH2:13][CH2:12][NH2:11])[CH3:24]

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 2733930(S)-2-Hydroxy-4-(((phenylmethoxy)carbonyl)amino)butyric acid

Product 1

HCID 1317179804-Amino-2(S)-hydroxybutyric acid ethyl ester, hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Add 4-benzyloxycarbonylamino-2(S)-hydroxybutyric acid (2.57 g) to absolute ethanol (30 ml) containing thionyl chloride (2.0 ml) and heat the resulting mixture under reflux for 20 hours. Cool, filter and concentrate the reaction mixture in vacuo to give a pale yellow oil. Chromatograph this oil on a column of silica gel (500 ml) using ethyl acetate as eluant to obtain a yellow oil, [α]D26 =+0.4° (MeOH). Hydrogenate the product (1.4 g) in absolute ethanol (50 ml) containing 10% Pd/C (0.50 g) at 50 psi for 2 hours. Filter the mixture and concentrate the mixture in vacuo to give the title compound as an oil.

Workup

  1. temperatureheat the resulting mixture
  2. temperatureunder reflux for 20 hours
  3. temperatureCool
  4. filtrationfilter
  5. concentrationconcentrate the reaction mixture in vacuo
  6. customto give a pale yellow oil
  7. filtrationFilter the mixture
  8. concentrationconcentrate the mixture in vacuo

Sources & evidence

ORD record
ord-d63c0d21baef430cb46e78496d6a25ba
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Linked notes

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