Sodium Hydroxide → 6-[2-Methyl-4-[alpha,alpha-diethyl-3-methyl-4-[(E)-3-ethyl-3-hydroxy-1-pentenyl]benzyl]phenyl]pyridine-3-acetic acid

HRID 546958Notes

Reaction equation

HRID 546958 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH2:36][CH3:37])([C:21]3[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]([CH2:33][CH3:34])([OH:32])[CH2:30][CH3:31])=[C:23]([CH3:35])[CH:22]=3)[CH2:19][CH3:20])=[CH:14][C:13]=2[CH3:38])=[CH:10][CH:11]=1)C.[OH-].[Na+].P([O-])(O)(O)=O.[Na+]>CO.O1CCCC1>[CH2:19]([C:18]([C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[CH:7][C:6]([CH2:5][C:4]([OH:39])=[O:3])=[CH:11][CH:10]=2)=[C:13]([CH3:38])[CH:14]=1)([C:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]([CH2:30][CH3:31])([OH:32])[CH2:33][CH3:34])=[C:23]([CH3:35])[CH:22]=1)[CH2:36][CH3:37])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 23672064Monosodium phosphateHCID 57709093[6-(4-{1-Ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

Product 1

HCID 159422646-[2-Methyl-4-[alpha,alpha-diethyl-3-methyl-4-[(E)-3-ethyl-3-hydroxy-1-pentenyl]benzyl]phenyl]pyridine-3-acetic acidYield 65%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[6-(4-{1-Ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-2-methyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (Example 81-(1); 24.6 mg, 0.047 mmol) was dissolved in methanol/tetrahydrofuran=1:1 (1 mL). A 1 N sodium hydroxide aqueous solution (0.1 mL) was added, and the mixture was stirred at room temperature for one hour. A 30% sodium dihydrogenphosphate aqueous solution (0.3 mL) was added to the reaction mixture, and then the reaction mixture was concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/1) to give the title compound (15 mg, 65%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by preparative TLC (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-f3d37c8d858d498495b0ba8210278d95
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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