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

HRID 63019Notes

Reaction equation

HRID 63019 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C([O:18][C:19](=[O:30])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([Cl:29])[CH:23]=1)C>>[Cl:29][C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][C:19]([OH:30])=[O:18])[CH:27]=[CH:26][C:25]=1[O:28][CH2:2][C:3]1[C:4]([S:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 68766162Ethyl 3-(3-chloro-4-hydroxyphenyl)propanoateHCID 901180413-Chloromethyl-2-cyclopentylsulfanyl-6-methyl-pyridine

Product 1

HCID 901181343-[3-Chloro-4-(2-cyclopentylsulfanyl-6-methyl-pyridin-3-ylmethoxy)-phenyl]-propionic acidYield 58%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-6-methyl-pyridine (35 mg, 0.15 mmol) obtained in Step C of Preparation Example 36 and 3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester (36 mg, 0.17 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 (30 mg, 58%).

Workup

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

Sources & evidence

ORD record
ord-c10ee6611019421dbe187f95e7e87b03
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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