Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate → Di-tert-butyl (4S)-4-(4-aminobenzyl)-N-(tert-butoxycarbonyl)-L-glutamate

HRID 591260Notes

Reaction equation

HRID 591260 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:10][C@H:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=1)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][C@@H:9]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:25][CH:24]=1

Participants

4

Reactant 1

HCID 89136291Di-tert-butyl (4S)-N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate

Product 1

HCID 89136283Di-tert-butyl (4S)-4-(4-aminobenzyl)-N-(tert-butoxycarbonyl)-L-glutamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2.35 g (4.3 mmol) di-tert-butyl (4S)—N-(tert-butoxycarbonyl)-4-(4-nitrobenzyl)-L-glutamate in 50 mL methanol and under argon atmosphere palladium (10% on charcoal) was added and the suspension hydrogenated overnight at room temperature. The reaction mixture was filtered, the solvent evaporated and the residue was chromatographed on silica gel using a hexane/ethyl acetate gradient, and the appropriate fractions were combined and concentrated.

Workup

  1. customthe suspension hydrogenated overnight
  2. customat room temperature
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent evaporated
  5. customthe residue was chromatographed on silica gel using a hexane/ethyl acetate gradient
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3afdcd2b3bb3487390f10fab5d309632
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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