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
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.
Workup
- temperaturethe resulting solution was gently heated
- temperatureunder reflux for 4 hours
- extractionthe product thoroughly extracted into methylene chloride
- washThe combined methylene chloride extracts were washed with cold water, brine
- dry with materialdried with magnesium sulfate
- customRemoval of the solvent under vacuum
Sources & evidence
- ORD record
- ord-90ed32b7618141b3b534f97a60e43dfe
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212195
Reaction notes
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