[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester → [(1S*,2S*,4R*)-4-Butylcarbamoyl-2-hydroxy-1-(3-hydroxy-benzyl)-pentyl]-carbamic acid tert-butyl ester

HRID 1432338Notes

Reaction equation

HRID 1432338 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28]CC2C=CC=CC=2)[CH:23]=1)[C@@H:9]([OH:20])[CH2:10][C@H:11]([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([OH:28])[CH:23]=1)[C@@H:9]([OH:20])[CH2:10][C@H:11]([C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH3:12])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 1

HCID 11648991[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester

Product 1

HCID 68887602[(1S*,2S*,4R*)-4-Butylcarbamoyl-2-hydroxy-1-(3-hydroxy-benzyl)-pentyl]-carbamic acid tert-butyl esterYield 93.8%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

[(1S*,2S*,4R*)-1-(3-Benzyloxy-benzyl)-4-butylcarbamoyl-2-hydroxy-pentyl]-carbamic acid tert-butyl ester (240 mg, 0.48 mmol) is hydrogenated (5 atm H2) at rt with 10% Pd/C (Engelhard 4505, 60 mg) for 2 h. The catalyst is filtered off and after evaporation the residue is purified by chromatography on silica (Flashmaster, DCM to DCM/methanol 85/15) to give a white foam (184 mg).

Workup

  1. customat rt
  2. customfor 2 h
  3. filtrationThe catalyst is filtered off
  4. customafter evaporation the residue
  5. customis purified by chromatography on silica (Flashmaster, DCM to DCM/methanol 85/15)

Sources & evidence

ORD record
ord-a557e1f18f3c402f8d6db461937ddf28
Source dataset
uspto-grants-2009_11
Patent number
US07612054B2

Reaction notes

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