HCID 21830402, compound → HCID 21830412, compound

HRID 1601051Notes

Reaction equation

HRID 1601051 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:16][C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][C:29]=1[N+:30]([O-])=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[NH2:30][C:29]1[CH:28]=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:18][C:17]=1[CH2:16][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10]

Participants

4

Reactant 1

HCID 21830402HCID 21830402, compound

Product 1

HCID 21830412HCID 21830412, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of tert-butyl 3-[[bis-(t-butoxycarbonyl)]amino]methyl-4-nitrobenzoate (4.2 g, 9.3 mmol) in ethanol (150 mL) was hydrogenated at 40 psi in the presence of 10% Pd on C (0.40 g). After 30 minutes, catalyst was filtered and solvent removed to give the title compound in essentially quantitative yield: MS (ES) m/e 423 (M+H)+ ; 1H NMR (400 MHz, CDCl3) δ 7.82 (s, 1H), 7.71 (d, J=8.4 Hz, 1H), 6.56 (d, J=8.4 Hz, 1H), 4.92 (br s, 2H), 4.68 (s, 2H), 1.62 (s, 9H), 1.49 (s, 18H).

Workup

  1. filtrationcatalyst was filtered
  2. customsolvent removed

Sources & evidence

ORD record
ord-4fb9b10e42c14138ac9bd98d83ed25b6
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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