4-(2-Bicyclo[2.2.1]hept-7-yl-1-methoxycarbonyl-ethylamino)-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester → 3-Bicyclo[2.2.1]hept-7-yl-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

HRID 19364Notes

Reaction equation

C([O:3][C:4](=O)[CH:5]=[C:6]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29])[CH2:7][NH:8][CH:9]([C:18]([O:20][CH3:21])=[O:19])[CH2:10][CH:11]1[CH:15]2[CH2:16][CH2:17][CH:12]1[CH2:13][CH2:14]2)C>C(#N)C>[CH3:21][O:20][C:18](=[O:19])[CH:9]([N:8]1[CH2:7][C:6]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[CH:5][C:4]1=[O:3])[CH2:10][CH:11]1[CH:12]2[CH2:13][CH2:14][CH:15]1[CH2:16][CH2:17]2

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 4-(2-bicyclo[2.2.1]hept-7-yl-1-methoxycarbonyl-ethylamino)-3-(2-chloro-phenoxy)-but-2-enoic acid ethyl ester (83 mg, 0.19 mmol) in acetonitrile (2 mL) was placed in a sealed microwave reaction tube and heated in a microwave reactor at 150° C. for 6 h. The mixture was concentrated in vacuo and purified by AnaLogix IntelliFlash flash chromatography (4 g column, 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) which afforded 3-bicyclo[2.2.1]hept-7-yl-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (35 mg, 23%, over two steps) as a yellow oil.

Workup

concentrationThe mixture was concentrated in vacuo
custompurified by AnaLogix IntelliFlash flash chromatography (4 g column, 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-706618dfcd0e44a3b81fe9ec09c14901
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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