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

HRID 19347Notes

Reaction equation

C[O:2][C:3](=[O:26])[CH:4]([N:12]1[CH2:16][C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][C:13]1=[O:25])[CH2:5][CH:6]([CH3:11])[C:7]([F:10])([F:9])[F:8].O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:17][C:15]1[CH2:16][N:12]([CH:4]([CH2:5][CH:6]([CH3:11])[C:7]([F:10])([F:9])[F:8])[C:3]([OH:26])=[O:2])[C:13](=[O:25])[CH:14]=1

Participants

Conditions

Temperature: 25 °C

Procedure

In a flask was placed 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-methyl-pentanoic acid methyl ester (614 mg, 1.56 mmol) dissolved in tetrahydrofuran (10 mL). To this mixture at 25° C. was added a solution of lithium hydroxide monohydrate (131 mg, 3.13 mmol) in water (10 mL). The mixture was then stirred for 2 h at 25° C. After such time, the mixture was treated with a 1N aqueous hydrochloric acid solution until pH=2 and extracted with ethyl acetate (3×20 mL). The organics were combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-methyl-pentanoic acid (575 mg, 98%) as a yellow-orange solid.

Workup

customIn a flask was placed
extractionextracted with ethyl acetate (3×20 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f7b1b74388bc47e891542e2228342772
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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