(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-nitro-1,1'-biphenyl-4-yl)acetic acid → (2-Amino-4'-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetic acid

HRID 2076648Notes

Reaction equation

HRID 2076648 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:34]([OH:35])=[C:33]([C:36]([F:39])([F:38])[F:37])[CH:32]=[CH:31][C:9]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([OH:27])=[O:26])=[CH:20][C:19]=2[N+:28]([O-])=O)=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[NH2:28][C:19]1[CH:20]=[C:21]([CH2:24][C:25]([OH:27])=[O:26])[CH:22]=[CH:23][C:18]=1[C:15]1[CH:14]=[CH:13][C:12]([O:11][CH2:10][C:9]2[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:39])[F:37])=[C:34]([OH:35])[C:8]=2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:17][CH:16]=1

Participants

3

Reactant 1

HCID 11570241(4'-{[2-(tert-Butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-nitro-1,1'-biphenyl-4-yl)acetic acid

Product 1

HCID 11540867(2-Amino-4'-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Rhodium-alumina (Rh 5%) (100 mg) was added to a solution of (4′-{[2-(tert-butoxycarbonyl)-3-hydroxy-4-(trifluoromethyl)benzyl]oxy}-2-nitro-1,1′-biphenyl-4-yl)acetic acid (130 mg, 0.237 mmol) obtained in Example (37-2) in methanol (4 ml), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 days. The insolubles were removed by filtration through Celite and the filtrate was concentrated. The obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=20/1) to give the title compound as a yellow amorphous compound (63 mg, yield: 51%).

Workup

  1. customThe insolubles were removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=20/1)

Sources & evidence

ORD record
ord-c49fa2290e5f49ed8de0e01bab4f3169
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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