Sodium Methoxide → Sodium 3-cyclopropyl-3-(3-(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoate

HRID 1049413Notes

Reaction equation

HRID 1049413 reaction equation
C[O-].[Na+:3].[CH:4]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=4[F:34])=[C:22]([CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:21]=3)[CH:13]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH2:6][CH2:5]1>CO>[CH:4]1([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:27]=4[F:34])=[C:22]([CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[CH:21]=3)[CH:13]=2)[CH2:8][C:9]([O-:11])=[O:10])[CH2:5][CH2:6]1.[Na+:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 1177596393-Cyclopropyl-3-(3-(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoic acid

Product 1

HCID 117759638Sodium 3-cyclopropyl-3-(3-(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoateYield 94.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methoxide (100 mg) in methanol was added to a solution of 3-cyclopropyl-3-(3-(((2-(2,2-dimethylpropyl)-2′-fluoro-5′-methoxybiphenyl-4-yl)oxy)methyl)phenyl)propanoic acid (255 mg) in methanol (2.5 mL), and the mixture was stirred at room temperature for 5 min. The reaction mixture was concentrated under reduced pressure to give the title compound (252 mg) as a white amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-65b76604a3154e108dbdb920c8ad4039
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

Loading…