反应详情

To a solution of mono-N-Boc-S-methylisothiourea (Preparation C, 764 mg, 4.0 mmol) and DIPEA (3.0 mL) in CH2Cl2 (8.0 mL) was added trifluoroacetic anhydride (924 mg, 4.4 mmol). The mixture was stirred at rt for 30 min, and then N-(4-(aminomethyl)-2,6-dichlorophenyl)acetamide (930 mg, 4.0 mmol) was added. The resulting mixture was stirred at rt overnight. The solvent was removed. Then 15 mL of MeOH and K2CO3 (1.2 g) were added. After stirring at rt for 30 min, the MeOH was removed. 50 mL of HCl (1 N) was added, and the mixture was washed with Et2O (50 mL) and then neutralized with 50% NaOH to pH=12. The aqueous layer was then extracted with EtOAc (2×100 mL). The organic layer was dried and concentrated to give 1.1 g (yield 73%) of the title compound. MS (ESI) (M+H)+=375.06. 1H NMR (500 MHz, CD3OD) δ 7.39 (s, 2 H), 4.41 (s, 2 H), 2.19 (s, 3 H), 1.45 (s, 9 H).

1. stirringThe resulting mixture was stirred at rt overnight
2. customThe solvent was removed
3. additionThen 15 mL of MeOH and K2CO3 (1.2 g) were added
4. stirringAfter stirring at rt for 30 min
5. customthe MeOH was removed
6. addition50 mL of HCl (1 N) was added
7. washthe mixture was washed with Et2O (50 mL)
8. extractionThe aqueous layer was then extracted with EtOAc (2×100 mL)
9. customThe organic layer was dried
10. concentrationconcentrated