Ethanol → [1-(4'-{3-Methyl-4-[1-(3-phenyl-isoxazol-5-yl)-ethylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid

HRID 1183349Notes

Reaction equation

HRID 1183349 reaction equation
C([O:3][C:4](=[O:41])[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[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[NH:27][CH:28]([C:30]4[O:34][N:33]=[C:32]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[CH:31]=4)[CH3:29])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)C.CCO.[OH-].[Na+]>C1COCC1>[CH3:26][C:23]1[C:22]([NH:27][CH:28]([C:30]2[O:34][N:33]=[C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:31]=2)[CH3:29])=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:6]4([CH2:5][C:4]([OH:41])=[O:3])[CH2:7][CH2:8]4)=[CH:14][CH:13]=3)=[CH:16][CH:17]=2)[O:25][N:24]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 66581212[1-(4'-{3-Methyl-4-[1-(3-phenyl-isoxazol-5-yl)-ethylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester

Product 1

HCID 51348460[1-(4'-{3-Methyl-4-[1-(3-phenyl-isoxazol-5-yl)-ethylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

[1-(4′-{3-Methyl-4-[1-(3-phenyl-isoxazol-5-yl)-ethylamino]-isoxazol-5-yl}-biphenyl-4-yl)-cyclopropyl]-acetic acid ethyl ester (0.0861 g, 0.157 mmol) was dissolved in THF (2 mL) then EtOH (1 mL) and NaOH (3N aq., 0.157 mL, 0.472 mmol) was added and the reaction stirred at 60° C. overnight. The reaction was submitted to standard workup procedure and purified via preparatory HPLC (0.1% TFA/H2O/ACN) to afford the title compound.

Workup

  1. custompurified via preparatory HPLC (0.1% TFA/H2O/ACN)

Sources & evidence

ORD record
ord-1aa097555c9c44e1a6dfc738b6e94392
Source dataset
uspto-grants-2014_03
Patent number
US08664220B2

Reaction notes

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