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

HRID 852672노트

반응식

HRID 852672 반응식
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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-109bfa3d7c444289a3464acf8f579abe
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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