Reaction #43853

Reaction equation

(4-tert-Butoxycarbonylamino-2-nitro-phenylamino)-acetic acid tert-butyl ester

→

sub-title compound

(2-Amino-4-tert-butoxycarbonylamino-phenylamino)-acetic acid tert-butyl ester

Solvents

MeOH

Conditions

Workup

1. 1
   Otherpurged with N2
2. 2
   workup.ADDITIONPalladium on activated carbon (2.2 g, 10% by weight) was added
3. 3
   workup.ADDITIONthe reaction mixture was charged with a balloon of H2
4. 4
   Filtrationfiltered through a pad of celite
5. 5
   WashThe celite was washed with MeOH
6. 6
   Concentrationthe filtrate was concentrated

Procedure

(4-tert-Butoxycarbonylamino-2-nitro-phenylamino)-acetic acid tert-butyl ester (10.8 g, 29.4 mmol) was dissolved in MeOH (70 mL) and purged with N2. Palladium on activated carbon (2.2 g, 10% by weight) was added, and the reaction mixture was charged with a balloon of H2. The reaction mixture was stirred for 3 h at room temperature, and then filtered through a pad of celite. The celite was washed with MeOH, and the filtrate was concentrated to afford 2.1 g (22%—two steps) of the sub-title compound. MS calculated for C17H27N3O4+H: 338, observed: 338.

Source