Sodium Hydroxide → 2-Hydroxy-3-{4-[1-(4'-isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoylamino}-propionic acid

HRID 1160930Notes

Reaction equation

HRID 1160930 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([OH:37])[CH2:5][NH:6][C:7](=[O:36])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([C:26]3[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)=[C:21]([CH3:35])[CH:20]=2)[CH:15]([CH3:17])[CH3:16])=[CH:10][CH:9]=1.[OH-].[Na+]>CO>[OH:37][CH:4]([CH2:5][NH:6][C:7](=[O:36])[C:8]1[CH:9]=[CH:10][C:11]([CH:14]([O:18][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([C:26]3[CH:27]=[CH:28][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:31]=3)=[C:21]([CH3:35])[CH:20]=2)[CH:15]([CH3:16])[CH3:17])=[CH:12][CH:13]=1)[C:3]([OH:38])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671535972-Hydroxy-3-{4-[1-(4'-isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoylamino}-propionic acid methyl ester

Product 1

HCID 671536602-Hydroxy-3-{4-[1-(4'-isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoylamino}-propionic acidYield 63.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of isomer 1 of 2-Hydroxy-3-{4-[1-(4′-isopropyl-2,6-dimethyl-biphenyl-4-yloxy)-2-methyl-propyl]-benzoylamino}-propionic acid methyl ester (150 mg) in methanol (10 mL) is added sodium hydroxide (5 N aqueous, 1 mL) and stirred for 4 h. The reaction mixture is concentrated and acidified by 5 N HCl (1 mL), extracted with ethyl acetate. Combined organic layers are washed with water and brine, dried over sodium sulfate. Concentration gives the title compound (93 mg) as a white solid. MS (ES): 504.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. extractionextracted with ethyl acetate
  3. washCombined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationConcentration

Sources & evidence

ORD record
ord-42148f1e34a748dbbeb47c4862c8bc0c
Source dataset
uspto-grants-2010_10
Patent number
US07816557B2

Reaction notes

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