Sodium Hydroxide → 2-[4-(2-Cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid
Reaction equation
C[O:2][C:3]([CH:5]1[CH2:7][CH:6]1[C:8]1[CH:13]=[C:12]([F:14])[C:11]([O:15][CH2:16][C:17]2[C:18]([S:23][CH2:24][CH:25]3[CH2:27][CH2:26]3)=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:10]([F:28])[CH:9]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO>[CH:25]1([CH2:24][S:23][C:18]2[C:17]([CH2:16][O:15][C:11]3[C:12]([F:14])=[CH:13][C:8]([CH:6]4[CH2:7][CH:5]4[C:3]([OH:4])=[O:2])=[CH:9][C:10]=3[F:28])=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:27][CH2:26]1Participants
4
Procedure
After 2-[4-(2-cyclopropylmethylsulfanyl-pyridin-3-ylmethoxy)-3,5-difluoro-phenyl]-cyclopropane carboxylic acid methyl ester (13 mg, 0.031 mmol) obtained in Step A was dissolved in THF/MeOH (1 mL/1 mL), 10N sodium hydroxide solution (30 mg, 0.31 mmol) was added thereto, and the mixture was stirred at room temperature for 12 hours. After the termination of the reaction, the reactant was concentrated under reduced pressure, and the residue was diluted with water. The aqueous layer was added with 1N HCl to adjust the pH to 2˜3, and then extracted with EtOAc. The organic layer was dried with MgSO4, concentrated under reduced pressure, and purified by column chromatography (eluent, MeOH/DCM=5/95) to obtain the title compound (12 mg, 97%).