methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenyl acetylamino]-1-propoxy]benzoate → methyl (S)-3-amino-4-[2-[3-methoxy-4-[N'-(2-methylphenyl) ureido]phenylacetylamino]-1-propoxy]benzoate

HRID 354501Notes

Reaction equation

HRID 354501 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C@@H:16]([NH:18][C:19](=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])=[O:29])=[C:23]([O:38][CH3:39])[CH:22]=1)[CH3:17])[C:7]([O:9][CH3:10])=[O:8])([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C@@H:16]([NH:18][C:19](=[O:40])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])=[O:29])=[C:23]([O:38][CH3:39])[CH:22]=1)[CH3:17])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 86587800methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenyl acetylamino]-1-propoxy]benzoate

Product 1

HCID 86587799methyl (S)-3-amino-4-[2-[3-methoxy-4-[N'-(2-methylphenyl) ureido]phenylacetylamino]-1-propoxy]benzoateYield 82.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A stirred solution of methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate (310 mg, 0.56 mmol) in MeOH—THF (10 mL, 1:1, v/v) was hydrogenated over 5% Pd—C (50 mg, 16 wt %) overnight. The mixture was filtered to remove the catalyst and the filtrate was evaporated to give methyl (S)-3-amino-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate (240 mg) as a gum.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e235069386dc41da837a5c6611f237ee
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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