Methanol → (1-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-4-yl]-biphenyl-4-yl}-cyclopropyl)-acetic acid

HRID 919066Notes

Reaction equation

HRID 919066 reaction equation
C([O:3][C:4](=[O:38])[CH2:5][C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][N:24]=[CH:23][C:22]=4[CH:27]([OH:37])[CH2:28][CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)C.CO.O.O.[OH-].[Li+]>C1COCC1>[OH:37][CH:27]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:11]=[CH:10][C:9]([C:6]3([CH2:5][C:4]([OH:38])=[O:3])[CH2:8][CH2:7]3)=[CH:14][CH:13]=2)=[CH:16][CH:17]=1)[CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67958500(1-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-4-yl]-biphenyl-4-yl}-cyclopropyl)-acetic acid ethyl ester

Product 1

HCID 57386374(1-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-4-yl]-biphenyl-4-yl}-cyclopropyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1-{4′-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-4-yl]-biphenyl-4-yl}-cyclopropyl)-acetic acid ethyl ester (0.240 g, 0.475 mmol) was dissolved in THF (5 mL), MeOH (2 mL) and H2O (2 mL) then lithium hydroxide monohydrate (0.100 g, 2.38 mmol) was added. The reaction was stirred overnight at room temperature. The reaction was submitted to standard aqueous workup then triturated with CH2Cl2:hexanes to afford the product as a solid that was recovered by filtration.

Workup

  1. customthen triturated with CH2Cl2

Sources & evidence

ORD record
ord-cb9c74fff2694bc1881314e944c61f67
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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