Ethanolamine → 7-Hydroxycoumarin-4-acetic acid-(2-hydroxyethyl) amide
Reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:17][C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)=[CH:14][CH:15]=2)[O:10][C:9](=[O:29])[CH:8]=1.C(CN)O>CN(C=O)C>[OH:1][CH2:2][CH2:3][NH:4][C:5](=[O:30])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[O:10][C:9](=[O:29])[CH:8]=1Participants
4
Procedure
200 mg (0.85 mmole) of 7-hydroxycoumarin-4-methyl ester 2 (prepared as described in Scheme 1) was dissolved in 5 ml of dry DMF and stirred with 0.5 g (8.5 mmoles) of ethanolamine at room temperature for 52 hrs. The DMF was then evaporated from the dark brown solution. The residue obtained after further evaporation with methanol was dissolved in water and purified on a C-8 RP-HPLC column using a gradient of 5/95 CH3CN/water (0.1% TFA) to 30170 CH3CN/water (0.1% TFA) in 25.5 min. The peak eluting at 21.6 min was collected and lyophilized to give 0.16 g of an off-white powder MS: Mol. Formula, C13H13NO5 ; Calculated: 263.26, found (M+H)+ 264.2.