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

HRID 19340Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid methyl ester (212 mg, 0.58 mmol) in a 1:1 solution of tetrahydrofuran:water (8 mL) was treated with lithium hydroxide monohydrate (55 mg, 1.16 mmol) and stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with water (10 mL) and the pH adjusted to pH=4 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layers were then dried over sodium sulfate and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4,4,4-trifluoro-butyric acid (149 mg, 73%) as a white solid: HR-ES-MS m/z calculated for C14H11NO4ClF3 [M+Na]+ 372.0221, observed 372.0224.

Workup

concentrationAfter such time, the mixture was concentrated in vacuo
customto remove the tetrahydrofuran
additiondiluted with water (10 mL)
extractionextracted with ethyl acetate
dry with materialThe organic layers were then dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-be9a41f4a48f4aa2b47d5412ba70ab13
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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