Ethanol → N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide

HRID 852672ノート

反応式

HRID 852672 の反応式
C(OC(=O)[NH:10][CH2:11][C@@H:12]([OH:42])[C@@H:13]([NH:21][C:22]([C:24]1[CH:29]=[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[C:26]([N:36]2[CH2:40][CH2:39][CH2:38][C:37]2=[O:41])[CH:25]=1)=[O:23])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)C1C=CC=CC=1.CCO>[Pd].O>[NH2:10][CH2:11][C@@H:12]([OH:42])[C@@H:13]([NH:21][C:22](=[O:23])[C:24]1[CH:29]=[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:27]=[C:26]([N:36]2[CH2:40][CH2:39][CH2:38][C:37]2=[O:41])[CH:25]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 702EthanolHCID 69359603[(2R,3S)-2-Hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester

生成物 1

HCID 69357401N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide収率 66.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of [(2R,3S)-2-hydroxy-3-({1-[3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-phenyl]-methanoyl}-amino)-4-phenyl-butyl]-carbamic acid benzyl ester (D105) (820 mg, 1.4 mmol, 1 equiv), 10% palladium on charcoal (50% wet, 100 mg, 6% w/w), NH4CO2H (800 mg, 12.7 mmol, 9 equiv), EtOH (25 ml) and H2O (10 ml) was stirred at 60° C. for 1 h. The mixture was then cooled to room temperature and the catalyst was filtered off through a pad of celite. Most of the EtOH was removed in vacuo and the residue was partitioned between AcOEt and H2O. The aqueous phase was extracted with AcOEt. The combined organic phases were dried over MgSO4 and concentrated in vacuo to give N-((1S,2R)-3-amino-1-benzyl-2-hydroxy-propyl)-3-(2-oxo-pyrrolidin-1-yl)-5-pentyloxy-benzamide (420 mg, 66%) as a white solid. [M+H]+=454.0, RT=2.63 min

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationthe catalyst was filtered off through a pad of celite
  3. customMost of the EtOH was removed in vacuo
  4. customthe residue was partitioned between AcOEt and H2O
  5. extractionThe aqueous phase was extracted with AcOEt
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-109bfa3d7c444289a3464acf8f579abe
出典データセット
uspto-grants-2007_08
特許番号
US07253198B2

反応ノート

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