反应详情

Dissolve 3-(tert-butoxycarbonylamino-methyl)-benzoic acid methyl ester (2.80 g, 10.6 mmol) in dimethylformamide (60 mL). Add 60% sodium hydride dispersion in oil (0.52 g, 13 mmol). Stir for 1 hr. Add methyl iodide (0.81 mL, 13 mmol) and stir for additional 1 hr. Quench the reaction with water and concentrate. Partition the residue between ethyl acetate and water. Separate the organic layer and dry over sodium sulfate. Filter and concentrate. Purify the residue by chromatography (silica gel) eluting with 15-25% ethyl acetate/hexane to provide the title compound (1.70 g, 57%).

1. customQuench
2. customthe reaction with water
3. concentrationconcentrate
4. customPartition the residue between ethyl acetate and water
5. customSeparate the organic layer
6. dry with materialdry over sodium sulfate
7. filtrationFilter
8. concentrationconcentrate
9. customPurify the residue by chromatography (silica gel)
10. washeluting with 15-25% ethyl acetate/hexane