[CH:1]([C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[O:7][CH:8]([CH3:28])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([O:22]CC)=[O:21])=[CH:14][CH:13]=1)=[O:10])([CH3:3])[CH3:2].O.Cl>C(#N)C.[OH-].[Na+]>[CH:1]([C:4]1[CH:5]=[C:6]([CH:29]=[CH:30][CH:31]=1)[O:7][CH:8]([CH3:28])[C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([CH:18]([C:25]#[C:26][CH3:27])[CH2:19][C:20]([OH:22])=[O:21])=[CH:16][CH:17]=1)=[O:10])([CH3:2])[CH3:3]A solution of 156 mg of ethyl 3-{4-[2-(3-isopropylphenoxy)propionylamino]phenyl}-hex-4-ynoate in 7 ml of acetonitrile and 7 ml of 1 N NaOH (aq) was stirred at room temperature for 18 h. The reaction mixture was admixed with water and adjusted to pH=1 with 1 N HCl (aq) and then extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under high vacuum. This gave 109 mg of 3-{4-[2-(3-isopropylphenoxy)propionylamino]phenyl}hex-4-ynoic acid in 37% yield over the two stages.
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