反应详情

Methyl 4-aminomethylsalicylate hydrochloride (2.25 g, 10.3 mmoles) was suspended in anhydrous N,N-dimethylformamide (30 mL), and N,N-diisopropylethylamine (3.6 mL, 20.7 mmoles) was added, followed by N-tert-butoxycarbonyl-6-aminohexanoic acid succinimidyl ester (3.38 g, 10.3 mmoles). The mixture was stirred under dry nitrogen for 18 hours, during which time all solids dissolved. The solvent was then evaporated toleave a light brown syrup, which was partitioned between ethyl acetate (100mL) and 1M aqueous hydrochloric acid (100 mL). The layers were separated, and the ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and evaporated to an amorphous off-white solid. The solid was crystallizedform ethyl acetate/hexanes, filtered, and dried in vacuo to afford 3.25 g (80% yield) of methyl (N-tert-butoxycarbonyl-6-aminohexanoyl)-aminomethylsalicylate (m.p. 120°-121° C., open capillary, uncorrected).

1. dissolutiondissolved
2. customThe solvent was then evaporated
3. customa light brown syrup, which was partitioned between ethyl acetate (100mL) and 1M aqueous hydrochloric acid (100 mL)
4. customThe layers were separated
5. washthe ethyl acetate solution was washed with saturated aqueous sodium bicarbonate (100 mL) and saturated aqueous sodium chloride (100 mL)
6. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated to an amorphous off-white solid
9. filtrationfiltered
10. customdried in vacuo