2-Benzyloxycarbonylamino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl ester → 2-Amino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl ester

HRID 2088333Notes

Reaction equation

HRID 2088333 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH:5]([NH:19]C(OCC1C=CC=CC=1)=O)[CH2:6][CH2:7][C:8](=[O:18])[NH:9][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][OH:12])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:30])[CH:5]([NH2:19])[CH2:6][CH2:7][C:8](=[O:18])[NH:9][CH:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][OH:12])[CH3:2]

Participants

4

Reactant 1

HCID 687324842-Benzyloxycarbonylamino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl ester

Product 1

HCID 725709632-Amino-4-(1-ethoxycarbonyl-2-hydroxy-ethylcarbamoyl)-butyric acid ethyl esterYield 75.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (4) (11.4 g, 26.86 mmol) in ethanol (225 ml) containing 1.2 g 20% palladium on activated carbon (50% wet) was hydrogenated at 30 psi for 3 hrs. The catalyst was removed by filtration and the solution was washed with ethanol. The solvent was removed in a rotary evaporator. The residue was dried in a vacuum oven (50° C.) to produce (5) (5.86 g, 75%).

Workup

  1. customThe catalyst was removed by filtration
  2. washthe solution was washed with ethanol
  3. customThe solvent was removed in a rotary evaporator
  4. customThe residue was dried in a vacuum oven (50° C.)

Sources & evidence

ORD record
ord-76ab54455fcb4909b2385ece65fb1f96
Source dataset
uspto-grants-2013_05
Patent number
US08435956B2

Reaction notes

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