Hydrochloric Acid → [6-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid

HRID 546844Notes

Reaction equation

HRID 546844 reaction equation
[OH-].[Na+].O.C([O:6][C:7](=[O:42])[CH2:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:39][CH3:40])([C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]([OH:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:38])[CH:25]=3)[CH2:22][CH3:23])=[CH:17][C:16]=2[CH3:41])=[CH:13][CH:14]=1)C.Cl>CO>[CH2:22]([C:21]([C:18]1[CH:19]=[CH:20][C:15]([C:12]2[N:11]=[CH:10][C:9]([CH2:8][C:7]([OH:42])=[O:6])=[CH:14][CH:13]=2)=[C:16]([CH3:41])[CH:17]=1)([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH:32]([OH:37])[C:33]([CH3:35])([CH3:36])[CH3:34])=[C:26]([CH3:38])[CH:25]=1)[CH2:39][CH3:40])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57443486[6-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic Acid Ethyl Ester

Product 1

HCID 15941708[6-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixed solution of a 6 N sodium hydroxide aqueous solution (0.003 mL) with water (0.01 mL) was added to a solution of [6-(4-{1-ethyl-1-[4-(3-hydroxy-4,4-dimethyl-pentyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (Example 23-(3); 1.7 mg, 0.0032 mmol) in methanol (0.07 mL) at room temperature, and the mixture was stirred at room temperature for four hours. The mixture was acidified with a 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 (1.6 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-e90b1044119140fb826e9d384f1095d5
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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