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

HRID 1587982

反応式

HRID 1587982 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d63c0d21baef430cb46e78496d6a25ba
出典データセット
uspto-grants-1993_06
特許番号
US05219886

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