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

HRID 852672Notes

Reaction equation

HRID 852672 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-109bfa3d7c444289a3464acf8f579abe
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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