Tetrahydrofuran → HCID 66893479, compound

HRID 19325Notes

Reaction equation

C[O:2][C:3](=[O:23])[CH:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[CH:11][C:10]1=[O:22])[CH2:5][CH:6]([F:8])[F:7].O1CCCC1.O.[OH-].[Li+]>O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH2:13][N:9]([CH:4]([CH2:5][CH:6]([F:8])[F:7])[C:3]([OH:23])=[O:2])[C:10](=[O:22])[CH:11]=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-difluoro-butyric acid methyl ester (790 mg, 2.28 mmol) in a 1:1 solution of tetrahydrofuran:water (20 mL) was treated with lithium hydroxide monohydrate (230 mg, 4.56 mmol). The mixture was 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=5 with 1N aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was 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-difluoro-butyric acid (571 mg, 75%) as a cream colored solid: HR-ES-MS m/z calculated for C14H12NO4ClF2 [M+H]+ 332.0496, observed 332.0496.

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 layer was dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-eea6b4609f644230be57f49dd9978324
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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