Methanol → 3-{4-[1-(4'-tert-Butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoylamino}-propionic acid

HRID 642809Notes

Reaction equation

HRID 642809 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][NH:6][C:7](=[O:36])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:10][CH:9]=1.CO.[OH-].[Na+]>CCOC(C)=O>[C:32]([C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][CH:14]([C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][CH2:4][C:3]([OH:37])=[O:2])=[O:36])=[CH:9][CH:10]=3)[CH2:15][CH:16]([CH3:18])[CH3:17])=[CH:21][CH:22]=2)=[CH:31][CH:30]=1)([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68578347HCID 68578347, compound

Product 1

HCID 167388993-{4-[1-(4'-tert-Butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoylamino}-propionic acidYield 54.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-{4-[1-(4′-tert-butyl-biphenyl-4-ylamino)-3-methyl-butyl]-benzoylamino}-propionic acid methyl ester (30 mg) is taken into MeOH (10 mL), followed by the addition of 5N NaOH (1 mL). The reaction is stirred for 4 h, diluted with EtOAc, washed with aqueous HCl, and brine. The organic portion is dried over MgSO4, and concentrated to afford 16 mg of the titled compound. MS (ES): 487.3 [M+H]+.

Workup

  1. washwashed with aqueous HCl, and brine
  2. dry with materialThe organic portion is dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-152cf6baf7914a83aaf9ba5d465d1da9
Source dataset
uspto-grants-2010_04
Patent number
US07696248B2

Reaction notes

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