2-[2-(2-Chloro-phenoxy)-3-ethoxycarbonyl-allylamino]-5,5,5-trifluoro-4-methyl-pentanoic acid methyl ester → HCID 66894551, compound

HRID 19346Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:29])[CH:4]([NH:12][CH2:13][C:14]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])=[CH:15][C:16](OCC)=[O:17])[CH2:5][CH:6]([CH3:11])[C:7]([F:10])([F:9])[F:8]>C(#N)C>[CH3:1][O:2][C:3](=[O:29])[CH:4]([N:12]1[CH2:13][C:14]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:15][C:16]1=[O:17])[CH2:5][CH:6]([CH3:11])[C:7]([F:10])([F:9])[F:8]

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of 2-[2-(2-chloro-phenoxy)-3-ethoxycarbonyl-allylamino]-5,5,5-trifluoro-4-methyl-pentanoic acid methyl ester (726 mg, 1.66 mmol) in acetonitrile (5 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 140° C. for 2.5 h. The mixture was then concentrated in vacuo and purified by AnaLogix IntelliFlash flash chromatography (12 g column, 10% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) which afforded 2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-5,5,5-trifluoro-4-methyl-pentanoic acid methyl ester (379 mg, 58%) as a yellow oil.

Workup

concentrationThe mixture was then concentrated in vacuo
custompurified by AnaLogix IntelliFlash flash chromatography (12 g column, 10% ethyl acetate/hexanes to 40% ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-10a11285936243b4b79449905b6fa949
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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