Chloroform → HCID 19040993, compound

Reaction equation

[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:26])[CH3:25])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([OH:29])[CH:15]=2)=[CH:5][CH:4]=1)#[N:2].[OH-:32].[Na+].C(Cl)(Cl)Cl>CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:28]=[CH:27][C:17]([C:18]([N:20]([CH:24]([CH3:25])[CH3:26])[CH:21]([CH3:23])[CH3:22])=[O:19])=[C:16]([CH:15]=2)[O:29][C:17]([CH3:27])([CH3:16])[C:18]([OH:19])=[O:32])=[CH:30][CH:31]=1)#[N:2]

Participants

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide (5.7 g, 13.4 mmol) in 50 mL of acetone is treated with sodium hydroxide (5.4 g, 134 mmol) and heated to reflux. The reaction is treated slowly with chloroform (1.4 mL, 17.4 mmol) in 150 mL of acetone and refluxed for 4 hours. The reaction is concentrated in vacuo and the residue is partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting material is purified by chromatography on silica gel (200 g) with 0-10% methanol/ethyl acetate as the eluent to afford 2-[5-[5-(4-cyanophenoxy)pentyloxy]-2-[N,N -bis(1-methylethyl)aminocarbonyl]phenoxy]-2-methylpropanoic acid as a colorless foam.