Ethyl 3-(3-chloro-4-hydroxyphenyl)propanoate → 3-[3-Chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acid

HRID 63017Notes

Reaction equation

HRID 63017 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)[N:4]=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]([Cl:27])[CH:21]=1)C>>[Cl:27][C:22]1[CH:21]=[C:20]([CH2:19][CH2:18][C:17]([OH:28])=[O:16])[CH:25]=[CH:24][C:23]=1[O:26][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)[N:4]=1

Participants

3

Reactant 2

HCID 68766162Ethyl 3-(3-chloro-4-hydroxyphenyl)propanoateHCID 901181462-Chloromethyl-6-cyclobutylsulfanyl-pyridine

Product 1

HCID 901185013-[3-Chloro-4-(6-cyclobutylsulfanyl-pyridin-2-ylmethoxy)-phenyl]-propionic acidYield 63%

Procedure

2-Chloromethyl-6-cyclobutylsulfanyl-pyridine (34 mg, 0.17 mmol) obtained in Step C of Preparation Example 37 and 3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (43 mg, 0.19 mmol) obtained in Step C of Preparation Example 42 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (35 mg, 63%).

Workup

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

Sources & evidence

ORD record
ord-0fee3e07988c4ea194d9ef330b69df83
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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