Water → HCID 178461461, compound

HRID 19302Notes

Reaction equation

C[O:2][C:3](=[O:25])[CH:4]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:5][C@H:6]1[CH2:9][C@H:8]([CH3:10])[CH2:7]1.O.O.[OH-].[Li+]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([CH:4]([CH2:5][C@H:6]2[CH2:7][C@H:8]([CH3:10])[CH2:9]2)[C:3]([OH:25])=[O:2])[C:12](=[O:24])[CH:13]=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]-3-(trans-3-methyl-cyclobutyl)-propionic acid methyl ester (107 mg, 0.29 mmol) dissolved in a 1:1 solution of tetrahydrofuran:water (8 mL). To this mixture was added lithium hydroxide monohydrate (25 mg, 0.58 mmol) and the resulting mixture stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and partioned between 1N aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL). The organic layer was separated and dried over sodium sulfate and concentrated in vacuo to afford 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(trans-3-methyl-cyclobutyl)-propionic acid (102 mg, 100%) as a light amber semi-solid: HR-ES-MS m/z calculated for C18H20NO4Cl [M+H]+ 350.1154, observed 350.1154.

Workup

customIn a flask was placed
concentrationAfter such time, the mixture was concentrated in vacuo
customto remove the tetrahydrofuran
customThe organic layer was separated
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-07c9b277403744c4a5b41286252054d0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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