HCID 53980786, compound → N-(2,6-dichlorobenzoyl)-3-amino-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

HRID 24686Notes

Reaction equation

HRID 24686 reaction equation
[CH3:1][O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[C:19]([N+:33]([O-])=O)[CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]>CO.[Ni]>[CH3:1][O:2][C:3](=[O:36])[C@H:4]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:24]=2[O:31][CH3:32])=[C:19]([NH2:33])[CH:18]=1)[NH:5][C:6](=[O:15])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14]

Participants

4

Reactant 1

HCID 53980786HCID 53980786, compound

Product 1

HCID 53814367N-(2,6-dichlorobenzoyl)-3-amino-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl esterYield 83.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(2,6-dichlorobenzoyl)-3-nitro-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (1.07 g) in MeOH (15 mL) was added Raney-Ni (100 mg) and H2 gas was bubbled through the mixture for 15 min. The mixture was filtered through Celite and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 1:1) to give N-(2,6-dichlorobenzoyl)-3-amino-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (845 mg). ESMS: m/z 503 (MH+).

Workup

  1. customwas bubbled through the mixture for 15 min
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel; eluent: hexane to hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-7ace740a70e045ed8735978d421177c7
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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