Sodium Hydroxide → 1-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-2-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

HRID 919056Notes

Reaction equation

HRID 919056 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[C:26]([CH:27]([OH:37])[CH2:28][CH2:29][CH2:30][C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)=[CH:25][CH:24]=[CH:23][N:22]=4)=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C1COCC1.CCO>[OH:37][CH:27]([C:26]1[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]4)=[CH:14][CH:13]=3)=[CH:16][CH:17]=2)=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:28][CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 679578571-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-2-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 573861181-{4'-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-2-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

1-{4′-[3-(1-Hydroxy-4-phenyl-butyl)-pyridin-2-yl]-biphenyl-4-yl}-cyclopropanecarboxylic acid ethyl ester (0.258 g, 0.52 mmol) was dissolved in THF (2 mL) and EtOH (1 mL). NaOH (3N aq., 1.1 eq.) was added and the reaction stirred at 45° C. overnight. The reaction was concentrated to dryness, diluted with H20, washed with EtOAc, acidified and extracted with EtOAc. The solution was dried and concentrated to yield the title compound.

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. additiondiluted with H20
  3. washwashed with EtOAc
  4. extractionextracted with EtOAc
  5. customThe solution was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2b6b2dea05754117892db353802bac4c
Source dataset
uspto-grants-2016_03
Patent number
US09272990B2

Reaction notes

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