Ethanol → (S)-isoserine ethyl ester hydrochloride

HRID 1587981노트

반응식

HRID 1587981 반응식
S(Cl)([Cl:3])=O.COC1C=CC(COC([NH:15][CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[OH:18])=O)=CC=1.[CH2:24](O)[CH3:25]>>[ClH:3].[CH2:24]([O:21][C:19](=[O:20])[C@@H:17]([OH:18])[CH2:16][NH2:15])[CH3:25]

참가 물질

4

반응물 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 127738164-methoxybenzyloxycarbonyl-(S)-isoserine

생성물 1

HCID 86746976(S)-isoserine ethyl ester hydrochloride

실험 절차

At 0°-5°, add thionyl chloride (2.80 ml) dropwise to N-(4-methoxybenzyloxycarbonyl)-(S)-isoserine (5.0 g) in absolute ethanol (100 ml). Heat the mixture under reflux for 1 hour and stir for 20 hours at room temperature. Concentrate the reaction mixture in vacuo and pour the reaction mixture into diethyl ether (300 ml), and filter the solid. Wash the solid with diethyl ether and dry in vacuo to give the title compound, an amber oil, [α]D26 =-19.8° (MeOH).

후처리

  1. temperatureHeat the mixture
  2. temperatureunder reflux for 1 hour
  3. concentrationConcentrate the reaction mixture in vacuo
  4. additionpour the reaction mixture into diethyl ether (300 ml)
  5. filtrationfilter the solid
  6. washWash the solid with diethyl ether
  7. customdry in vacuo

출처 및 근거

ORD 기록
ord-61d0b6dc72a04ba68549abe8b776d6d3
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05219886

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