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

HRID 1914344Notes

Reaction equation

HRID 1914344 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-bc36bd1ba75a4361a48061a7b0ebe1f1
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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