Ethyl 3-(4-hydroxy-3-methoxyphenyl)propionate → 3-[4-(2-Isopropylsulfanyl-pyridin-3-ylmethoxy)-3-methoxy-phenyl]-propionic acid

HRID 62944Notes

Reaction equation

HRID 62944 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]([CH3:12])[CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:15][C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([O:26][CH3:27])[CH:20]=1)C>>[CH:10]([S:9][C:4]1[C:3]([CH2:2][O:25][C:22]2[CH:23]=[CH:24][C:19]([CH2:18][CH2:17][C:16]([OH:28])=[O:15])=[CH:20][C:21]=2[O:26][CH3:27])=[CH:8][CH:7]=[CH:6][N:5]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 123548Ethyl 3-(4-hydroxy-3-methoxyphenyl)propionateHCID 538166813-Chloromethyl-2-isopropylsulfanyl-pyridine

Product 1

HCID 901181723-[4-(2-Isopropylsulfanyl-pyridin-3-ylmethoxy)-3-methoxy-phenyl]-propionic acidYield 72%

Procedure

3-Chloromethyl-2-isopropylsulfanyl-pyridine (33 mg, 0.16 mmol) obtained in Step C of Preparation Example 1 and 3-(4-hydroxy-3-methoxy-phenyl]-propionic acid ethyl ester (40 mg, 0.17 mmol) obtained in Step C of Preparation Example 38 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (34 mg, 72%).

Workup

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

Sources & evidence

ORD record
ord-6b26cb92ae75431990c9aa3a5325f082
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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