Ethyl 3-(4-hydroxy-3-methoxyphenyl)propionate → 3-[4-(6-Isopropylsulfanyl-pyridin-2-ylmethoxy)-3-methoxy-phenyl]-propionic acid

HRID 62951Notes

Reaction equation

HRID 62951 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([S:9][CH:10]([CH3:12])[CH3:11])[N:4]=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:5]1[N:4]=[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]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 123548Ethyl 3-(4-hydroxy-3-methoxyphenyl)propionateHCID 901181412-Chloromethyl-6-isopropylsulfanyl-pyridine

Product 1

HCID 742227063-[4-(6-Isopropylsulfanyl-pyridin-2-ylmethoxy)-3-methoxy-phenyl]-propionic acidYield 61%

Procedure

2-Chloromethyl-6-isopropylsulfanyl-pyridine (32 mg, 0.15 mmol) obtained in Step C of Preparation Example 16 and 3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester (39 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 (30 mg, 61%).

Workup

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

Sources & evidence

ORD record
ord-d8a92536a69142f0bf39c2d072f12493
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

Loading…