Hydrochloric Acid → (4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)-acetic Acid

HRID 546914Notes

Reaction equation

HRID 546914 reaction equation
[OH-].[Na+].O.C[O:5][C:6](=[O:42])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH2:38][CH3:39])([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:25]([CH3:37])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:40])=[CH:10][C:9]=1[F:41].Cl>CO>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:42])=[O:5])=[C:9]([F:41])[CH:10]=2)=[C:15]([CH3:40])[CH:16]=1)([C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH:31]([OH:36])[C:32]([CH3:34])([CH3:35])[CH3:33])=[C:25]([CH3:37])[CH:24]=1)[CH2:38][CH3:39])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57709127HCID 57709127, compound

Product 1

HCID 15941991(4'-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)-acetic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixed solution of a 6 N sodium hydroxide aqueous solution (0.011 mL) with water (0.032 mL) was added to a solution of (4′-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 60-(2); 8.5 mg, 0.016 mmol) in methanol (0.22 mL) at room temperature, and the mixture was stirred at room temperature for six hours. The mixture was acidified with dilute hydrochloric acid aqueous solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give the title compound (8 mg, 100%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-750467afc61b4ec19b0d685d22b58841
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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