Water → (S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester

HRID 655540노트

반응식

HRID 655540 반응식
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([N:6]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7][CH:8](OC)[O:9]C)[CH3:5].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CC(=O)CC>[CH3:1][O:2][C:3](=[O:23])[C@@H:4]([N:6]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:7][CH:8]=[O:9])[CH3:5]

참가 물질

5

반응물 3

HCID 962WaterHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67074039(S)-2-[Benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester

생성물 1

HCID 86638111(S)-2-[Benzyloxycarbonyl-(2-oxo-ethyl)-amino]-propionic acid methyl ester수율 108.8%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

A solution of (S)-2-[benzyloxycarbonyl-(2,2-dimethoxy-ethyl)-amino]-propionic acid methyl ester (26.0 g, 80.0 mmol) and pyridinium toluene-4-sulfonate (10.0 g, 40.0 mmol) in 2-butanone (260 mL) and water (8.6 mL, 0.48 mol) was heated under reflux for 16 h, then the solution was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated to afford the title compound (24.3 g), which was directly used in the next step. Yellow oil, MS (ISP)=348.3 (M+Na)+.

후처리

  1. temperatureunder reflux for 16 h
  2. customthe solution was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-4b3a9428721846aeaa2780f1ac2d74ea
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071586B2

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