Tetrahydrofuran → 3-(2,6-Dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid

HRID 19344Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (56 mg, 0.13 mmol) in a 1:1 solution of tetrahydrofuran:water (4 mL) was treated with lithium hydroxide monohydrate (11 mg, 0.26 mmol). The mixture was then stirred for 1 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and then diluted with 1N aqueous hydrochloric acid until the pH was acidic and then extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford 3-(2,6-dichloro-phenyl)-2-[4-(2,6-difluoro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (40 mg, 74%) as a tan solid: HR-ES-MS m/z calculated for C19H13NO4Cl2F2 [M+H]+ 428.0263, observed 428.0263.

Workup

concentrationAfter such time, the mixture was concentrated in vacuo
customto remove the tetrahydrofuran
additiondiluted with 1N aqueous hydrochloric acid until the pH
extractionextracted with ethyl acetate
dry with materialThe organic layers were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-90308d5bd24241f3af084306973d5996
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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