Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → 3-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-propionic acid

HRID 62958Notes

Reaction equation

HRID 62958 reaction equation
Cl[CH2:2][C:3]1[C:4]([S:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[CH:7][CH:8]=1.C([O:17][C:18](=[O:30])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([CH3:28])[C:22]=1[CH3:29])C>>[CH:10]1([S:9][C:4]2[C:3]([CH2:2][O:27][C:24]3[CH:25]=[CH:26][C:21]([CH2:20][CH2:19][C:18]([OH:30])=[O:17])=[C:22]([CH3:29])[C:23]=3[CH3:28])=[CH:8][CH:7]=[CH:6][N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 901182833-Chloromethyl-2-cyclopentylsulfanyl-pyridine

Product 1

HCID 742227923-[4-(2-Cyclopentylsulfanyl-pyridin-3-ylmethoxy)-2,3-dimethyl-phenyl]-propionic acidYield 96%

Procedure

3-Chloromethyl-2-cyclopentylsulfanyl-pyridine (28 mg, 0.10 mmol) obtained in Step C of Preparation Example 8 and 3-(4-hydroxy-2,3-dimethyl-phenyl)-propionic acid ethyl ester (27 mg, 0.12 mmol) obtained in Step D of Preparation Example 43 were used to react sequentially in the same manner as in Steps A and B of Example 1 to obtain the title compound (37 mg, 84%).

Workup

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

Sources & evidence

ORD record
ord-a8d1673aa42d417da8af1cededc866ff
Source dataset
uspto-grants-2016_09
Patent number
US09447044B2

Reaction notes

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