Sodium Hydroxide → [2-(4-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyrimidin-5-yl]-acetic Acid

HRID 546962Notes

Reaction equation

HRID 546962 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:41])[CH2:7][C:8]1[CH:9]=[N:10][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](/[CH:29]=[CH:30]/[C:31]([CH2:35][CH3:36])([OH:34])[CH2:32][CH3:33])=[C:25]([CH3:37])[CH:24]=3)[CH2:21][CH3:22])=[CH:16][C:15]=2[CH3:40])=[N:12][CH:13]=1)C>CO>[CH2:21]([C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:11]2[N:10]=[CH:9][C:8]([CH2:7][C:6]([OH:41])=[O:5])=[CH:13][N:12]=2)=[C:15]([CH3:40])[CH:16]=1)([C:23]1[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([CH2:32][CH3:33])([OH:34])[CH2:35][CH3:36])=[C:25]([CH3:37])[CH:24]=1)[CH2:38][CH3:39])[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57709187[2-(4-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyrimidin-5-yl]-acetic Acid Ethyl Ester

Product 1

HCID 57709069[2-(4-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyrimidin-5-yl]-acetic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide aqueous solution (0.10 mL) was added to a solution of [2-(4-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyrimidin-5-yl]-acetic acid ethyl ester (Example 83-(1); 26.8 mg, 0.0507 mmol) in methanol (0.68 mL) at room temperature, and the mixture was stirred at room temperature for three hours. The solvent was distilled off and saturated aqueous ammonium chloride solution was added to the residue, 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 (25 mg, 100%).

Workup

  1. distillationThe solvent was distilled off
  2. additionsaturated aqueous ammonium chloride solution was added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcb5db0dd05b43a3b65e195c304af381
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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