反应详情

To a solution of 3-{[(benzyloxy)carbonyl]amino}-N-(tert-butoxycarbonyl)alanine (10.0 g, 30.0 mmol) in DMF (100 mL) was added HATU (14.0 g, 36.0 mmol). After 2 hours, methylamine (4.1 g, 60 mmol) and triethylamine (15.0 g, 149 mol) were added. After 16 hours, the reaction mixture was diluted with water and the aqueous layer was extracted with ethyl acetate (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient) to give benzyl {2-[(tert-butoxycarbonyl)amino]-3-(methylamino)-3-oxopropyl}carbamate. MS ESI calc'd. for C17H26N3O5 [M+H]+ 352. found 352. 1H NMR (300 MHz, CDCl3) δ 7.33-7.31 (m, 5H), 6.59-6.57 (m, 1H), 5.69-5.66 (m, 1H), 5.42-5.39 (m, 1H), 5.14-5.05 (m, 2H), 4.19-4.16 (m, 1H), 3.63-3.41 (m, 2H), 2.78 (d, J=4.8 Hz, 3H), 1.43 (s, 9H).

1. waitAfter 16 hours
2. extractionthe aqueous layer was extracted with ethyl acetate (3×100 mL)
3. dry with materialThe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified via reverse phase HPLC (acetonitrile/water with 0.1% TFA, linear gradient)