Methyl 3-(3'-fluoro-4'-hydroxyphenyl)propionate → 3-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acid

HRID 63007Notes

Reaction equation

HRID 63007 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C[O:16][C:17](=[O:28])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:26][C:23]3[CH:24]=[CH:25][C:20]([CH2:19][CH2:18][C:17]([OH:28])=[O:16])=[CH:21][C:22]=3[F:27])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 22558806Methyl 3-(3'-fluoro-4'-hydroxyphenyl)propionateHCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 901181613-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-3-fluoro-phenyl]-propionic acidYield 85.6%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (0.032 g, 0.14 mmol) obtained in Step C of Preparation Example 8 and 3-(3-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (0.030 g, 0.14 mmol) obtained in Step C of Preparation Example 6 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (0.045 g, 84%).

Workup

  1. customto react sequentially in the same manner as in Steps A and B of Example 1

Sources & evidence

ORD record
ord-f0615f6857114b8eb11f44409fbf8a64
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…