反应详情

To a cooled (0° C.) solution of N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid (225 mg) in methanol (1 mL), was added (trimethylsilyl)diazomethane 2M in hexanes (840 μL) until persistence of the yellow colour. After 40 min, ethyl acetate (5 mL) and acetic acid (50 μL) were added, then, one minute later, a saturated aqueous solution of sodium hydrogen carbonate until pH=7. The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo to a residue. The residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm), using gradient elution with a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B) to give N-[2-(3,5-Bis-hydroxymethyl-phenoxy)-ethyl]-N-methyl-succinamic acid methyl ester (103 mg). LC/MS (Method A3): ES: m/z 348 (M+Na)+; m/z 326 (M+H)+ m/z 308 (M−H2O+H)+; RT=0.43 min

1. customone minute
2. extractionThe aqueous phase was extracted with ethyl acetate
3. washThe combined organic layers were washed with a saturated aqueous solution of sodium chloride
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo to a residue
6. customThe residue was purified by silica gel chromatography (Merck SuperVarioFlash 25 g column, Si60 15-40 μm)
7. washelution
8. additionwith a mixture of DCM (A)/MeOH (B), (gradient: 98% A: 2% B down to 90% A: 10% B)