2-[2-(2-Chloro-phenoxy)-3-ethoxycarbonyl-allylamino]-5,5,5-trifluoro-pentanoic acid methyl ester → HCID 66895286, compound

HRID 19318Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH:4]([NH:11][CH2:12][C:13]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])=[CH:14][C:15](OCC)=[O:16])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8]>C(#N)C>[CH3:1][O:2][C:3](=[O:28])[CH:4]([N:11]1[CH2:12][C:13]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])=[CH:14][C:15]1=[O:16])[CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8]

Participants

Conditions

Temperature: 180 °C

Procedure

A solution of 2-[2-(2-chloro-phenoxy)-3-ethoxycarbonyl-allylamino]-5,5,5-trifluoro-pentanoic acid methyl ester (1.43 g, 3.78 mmol) in acetonitrile (4 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 180° C. for 3 h. The mixture was then cooled and concentrated in vacuo with silica gel (3 g). Purification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) afforded 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-pentanoic acid methyl ester (1.02 g, 50% over two steps) as a an amber oil: HR-ES-MS m/z calculated for C16H15NO4ClF3 [M+H]+ 378.0715, observed 378.0716.

Workup

temperatureThe mixture was then cooled
concentrationconcentrated in vacuo with silica gel (3 g)
customPurification by Biotage flash chromatography (Aspire 40 g column, 16% ethyl acetate/hexanes to 50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-db41a9d2d83142b9b0415615370c628f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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