di t-butyl 4-nitrobenzylcarbonyl-L-glutamate → di t-butyl 4-aminobenzylcarbonyl-L-glutamate

HRID 619413Notes

Reaction equation

HRID 619413 reaction equation
[N+:1]([CH:4]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:5][C@@H:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[NH:7][C:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][CH:4]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:5][C@@H:6]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[NH:7][C:8]([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9]

Participants

4

Reactant 1

HCID 86748613di t-butyl 4-nitrobenzylcarbonyl-L-glutamate

Product 1

HCID 86748612di t-butyl 4-aminobenzylcarbonyl-L-glutamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of di t-butyl 4-nitrobenzylcarbonyl-L-glutamate (9.7 g) in ethyl acetate (200 ml) was hydrogenated over 30% Pd/C (900 mg). The mixture was then filtered through Celite and evaporated to yield a yellow oil (di t-butyl 4-aminobenzylcarbonyl-L-glutamate) which was used without further purification. NMR: 8.23(d)1H; 6.92(d)2H; 6.50(d)2H; 4.86(s)2H; 4.15(m)1H; 3.24(s)2H; 2.22(m)2H; 1.8(m)2H); 1.4(d)18H. Yield 8.2 g 90%.

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-253c9e21cddc40979d8aeed8435cd93e
Source dataset
uspto-grants-1999_09
Patent number
US05958971

Reaction notes

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