Hydrochloric Acid → HCID 86746857, compound

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]#[N:30])=[CH:19][CH:18]=2)[CH:7]=[C:8]([CH2:10][CH2:11]C(OC)=O)[CH:9]=1)[CH2:2][CH2:3][CH3:4].[OH-:31].[Na+].Cl.[CH3:34][OH:35]>>[CH2:1]([C:5]1[N:6]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]#[N:30])=[CH:21][CH:22]=2)[CH:7]=[C:8]([CH:10]([CH3:11])[C:34]([OH:35])=[O:31])[CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 14798Sodium Hydroxide

HCID 18946733HCID 18946733, compound

Product 1

HCID 86746857HCID 86746857, compound

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 3-[2-(n-butyl)-1-(2"-cyanobiphenyl-4'-ylmethyl)pyrrol-4-yl]propionate (AG) (5.8 g) (prepared, e.g., as described in Preparation 23), in methanol (100 ml) was added 10% sodium hydroxide solution (35 ml), and the resulting solution was gently heated under reflux for 4 hours. After cooling to 0° C., the solution was acidified to pH 6 with hydrochloric acid solution (6N), and the product thoroughly extracted into methylene chloride. The combined methylene chloride extracts were washed with cold water, brine, and then dried with magnesium sulfate. Removal of the solvent under vacuum gave 3-[(2-(n-butyl)-1-(2"-cyanobiphenyl-4'-ylmethyl)pyrrol-4-yl]propionic acid (5.51 g), a compound of Formula (AH), as a slightly pinkish gum.