Tetrahydrofuran → 2-[4-(2-Chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-trifluoromethyl-pentanoic acid

HRID 19315Notes

Reaction equation

C[O:2][C:3](=[O:29])[CH:4]([N:15]1[CH2:19][C:18]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[CH:17][C:16]1=[O:28])[CH2:5][CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([F:10])([F:9])[F:8].O1CCCC1.O.[OH-].[Li+]>O>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][C:18]1[CH2:19][N:15]([CH:4]([CH2:5][CH:6]([C:11]([F:13])([F:14])[F:12])[C:7]([F:9])([F:8])[F:10])[C:3]([OH:29])=[O:2])[C:16](=[O:28])[CH:17]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-trifluoromethyl-pentanoic acid methyl ester (48 mg, 0.11 mmol) in a 1:1 solution of tetrahydrofuran:water (2 mL) was treated with lithium hydroxide monohydrate (11 mg, 0.22 mmol) and stirred for 2 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with water and the pH adjusted to pH=6 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-trifluoromethyl-pentanoic acid (35 mg, 75%) as an off-white solid: HR-ES-MS m/z calculated for C16H12NO4ClF6 [M+H]+ 432.0432, observed 432.0433.

Workup

concentrationAfter such time, the mixture was concentrated in vacuo
customto remove the tetrahydrofuran
additiondiluted with water
extractionextracted with ethyl acetate
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-778b763a824c478b9f04024bdf351b7c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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