Hydrochloric Acid → HCID 86685706, compound

HRID 1844643Notes

Reaction equation

C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[CH2:15][N:14]=2)=[CH:9][C:8]=1[Cl:30])CCC.O.[OH-].[Li+].Cl>C1COCC1.O>[Cl:30][C:8]1[CH:9]=[C:10]([C:13]2[CH2:17][C:16]([C:22]3[CH:23]=[C:24]([Cl:29])[CH:25]=[C:26]([Cl:28])[CH:27]=3)([C:18]([F:19])([F:21])[F:20])[CH2:15][N:14]=2)[CH:11]=[CH:12][C:7]=1[C:6]([OH:31])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-chloro-4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-benzoic acid butyl ester (Example I16) (0.48 g) in THF (16 ml) and water (8 ml) was added lithium hydroxide monohydrate (103 mg). The reaction mixture was stirred at 50° C. for 20 hours. The reaction mixture was cooled to ambient temperature and diluted with water, acidified by addition of aqueous hydrochloric acid (1M) and extracted twice with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to give 2-chloro-4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-benzoic acid (459 mg). 1H-NMR (400 MHz, CDCl3): 8.15-7.40 (m, 6H), 4.95 (d, 1H), 4.30 (d, 1H), 3.85 (d, 1H), 3.35 (d, 1H) ppm.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted twice with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-3ce8adae63c3461a99e6c252072ff716
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946447B2

Reaction notes

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