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

HRID 1587982

반응식

HRID 1587982 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d63c0d21baef430cb46e78496d6a25ba
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05219886

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