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

HRID 655540ノート

反応式

HRID 655540 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4b3a9428721846aeaa2780f1ac2d74ea
出典データセット
uspto-grants-2011_12
特許番号
US08071586B2

反応ノート

読み込み中…