Methanol → HCID 54305290, compound

HRID 1741525Notes

Reaction equation

HRID 1741525 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[CH:30](CNC1C=CC=CC=1[N+]([O-])=O)[C:31]([OH:33])=[O:32])=O)(C)(C)C.[CH3:45]O>[Pd]>[CH3:45][O:33][C:31](=[O:32])[CH2:30][N:21]1[C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]1=2

Participants

5

Reactant 3

HCID 887MethanolHCID 15490830HCID 15490830, compoundHCID 22881946(2S)-3-[(2-aminophenyl)amino]-2-{[(tert-butoxy)carbonyl]amino}propanoic acid

Product 1

HCID 54305290HCID 54305290, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2(S)-tert-Butoxycarbonylamino-3-(2-aminophenyl-amino)-propionic acid. A mixture of 2-tert-Butoxycarbonylamino-3-(2-nitrophenylamino)propionic acid (12.65 g, 40.5 mmol) and 0.5 g of 10% Pd/C in 100 ml of methanol under hydrogen at 1 atmosphere was stirred for 4 hrs. The solution was filtered through Celite 545 and the filtrate evaporated in vacuo to afford 11.95 g of the title compound in quantitative yield as a dark brown solid that was used without purification. 1H NMR (CD3OD) δ6.75-6.70 (3H,m), 6.65-6.58 (1H, m), 4.35-4.3 1H, m), 3.6-3.38 (2H, m), 1.45 (9H, s).

Workup

  1. filtrationThe solution was filtered through Celite 545
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-54aeb370daf84b9eb83cab80761bf401
Source dataset
uspto-grants-1999_10
Patent number
US05973111

Reaction notes

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