Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoate → 3-[3-Chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acid

HRID 62969Notes

Reaction equation

HRID 62969 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:4]=1.C([O:17][C:18](=[O:30])[CH:19]([CH3:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([Cl:28])[CH:22]=1)C>>[Cl:28][C:23]1[CH:22]=[C:21]([CH2:20][CH:19]([CH3:29])[C:18]([OH:30])=[O:17])[CH:26]=[CH:25][C:24]=1[O:27][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:4]=1

Participants

3

Reactant 2

HCID 58566718Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoateHCID 901181812-Chloromethyl-6-cyclopentylsulfanyl-pyridine

Product 1

HCID 901183533-[3-Chloro-4-(6-cyclopentylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-2-methyl-propionic acidYield 85%

Procedure

2-Chloromethyl-6-cyclopentylsulfanyl-pyridine (37 mg, 0.16 mmol) obtained in Step C of Preparation Example 27 and 3-(3-chloro-4-hydroxy-phenyl)-2-methyl-propionic acid ethyl ester (43 mg, 0.17 mmol) obtained in Step B of Preparation Example 46 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (51 mg, 85%).

Workup

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

Sources & evidence

ORD record
ord-8029d151167847a691c158262a2a8087
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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