methyl N-(tert-butoxycarbonyl)-4-nitrophenylalaninate → Methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

HRID 1869779Notes

Reaction equation

HRID 1869779 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH3:13])=[O:11])=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 14054107methyl N-(tert-butoxycarbonyl)-4-nitrophenylalaninate

Product 1

HCID 22227788Methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[(tert-butoxycarbonyl)amino]-3-(4 nitrophenyl)propanoate 3 (69.4 g) and NH4HCO2 (6.5 equ.) in CH3OH (20 ml/g) is added 5% Pd/C (15% in weight, 10 g). The temperature rises to 40° C. and then decreases. After stirring for 2 h at room temperature, the solution is filtered over celite and the solvent is evaporated. The residue is diluted in AcOEt and washed 3 times with water. The organic phase is dried over MgSO4 and evaporated to dryness. No further purification is needed.

Workup

  1. customrises to 40° C.
  2. filtrationthe solution is filtered over celite
  3. customthe solvent is evaporated
  4. additionThe residue is diluted in AcOEt
  5. washwashed 3 times with water
  6. dry with materialThe organic phase is dried over MgSO4
  7. customevaporated to dryness
  8. customNo further purification

Sources & evidence

ORD record
ord-825211d88d6f47c2b0e783ebb76d99fd
Source dataset
uspto-grants-2009_12
Patent number
US07638630B2

Reaction notes

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