Lithium Hydroxide → 1-{4'-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopentanecarboxylic acid

HRID 557641Notes

Reaction equation

HRID 557641 reaction equation
C([O:3][C:4]([C:6]1([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:27][N:26]=[C:25]([CH3:28])[C:24]=4[NH:29][C:30]([O:32][C@@H:33]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH3:34])=[O:31])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5])C.[Li+].[OH-].CCOC(C)=O>O1CCOCC1>[CH3:28][C:25]1[C:24]([NH:29][C:30]([O:32][C@@H:33]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH3:34])=[O:31])=[C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:14]3[CH:13]=[CH:12][C:11]([C:6]4([C:4]([OH:5])=[O:3])[CH2:10][CH2:9][CH2:8][CH2:7]4)=[CH:16][CH:15]=3)=[CH:18][CH:19]=2)[O:27][N:26]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 666605231-{4'-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopentanecarboxylic acid ethyl ester

Product 1

HCID 498383011-{4'-[3-Methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopentanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

1-{4′-[3-methyl-4-((R)-1-phenyl-ethoxycarbonylamino)-isoxazol-5-yl]-biphenyl-4-yl}-cyclopentanecarboxylic acid ethyl ester (0.060 g, 0.11 mmol) in 1,4-dioxane (2 mL) was treated with 1N aqueous LiOH (1 mL), and the reaction was stirred at 60° C. overnight. Acidic work-up, followed by silica gel chromatography (0-50% EtOAc in hexanes) gave the title compound.

Sources & evidence

ORD record
ord-c3b34bf0314d44eab6368e17c46b0ab8
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

Loading…