反应详情

Ethyl chloroformate (1.26 mmol, 0.12 mL) and triethylamine (1.37 mmol, 0.19 mL) were added to a cooled (0° C.) solution of 3-[4-(2,3-Diphenylpropionylamino)phenyl]-2-propenoic acid (1.05 mmol, 0.39 g) in dry THF (10 mL), and the mixture was stirred for 10 min. The solid was filtered off, and O-(2-methoxy-2-propyl)hydroxylamine (3.15 mmol, 0.23 mL) was added to the filtrate. The solution was stirred for 15 min at 0° C., then was evaporated under reduced pressure, and the residue was diluted in methanol (10 mL). Amberlyst® 15 ion-exchange resin (105 mg) was added to the solution of the O-protected hydroxamate, and the mixture was stirred at room temperature for 1 h. After, the reaction was filtered and the filtrate was concentrated in vacuo to give the crude MC1895 which was purified by crystallization. 1H NMR (DMSO-d6) δ 3.05 (m, 1H, PhCH2), δ 3.60 (m, 1H, PhCH2), δ 3.75 (m, 1H, PhCHCO), δ 6.36 (d, 1H, PhCH═CHCOOEt), δ 7.15-7.70 (m, 15H, benzene protons and PhCH═CHCOOEt), δ 9.00 (s, 1H, OH), δ 10.23 (s, 1H, CONHPh), δ 10.85 (s, 1H, NHOH). Anal. C, H, N, O.

1. filtrationThe solid was filtered off
2. stirringThe solution was stirred for 15 min at 0° C.
3. customwas evaporated under reduced pressure
4. additionthe residue was diluted in methanol (10 mL)
5. additionAmberlyst® 15 ion-exchange resin (105 mg) was added to the solution of the O-protected hydroxamate
6. stirringthe mixture was stirred at room temperature for 1 h
7. filtrationAfter, the reaction was filtered
8. concentrationthe filtrate was concentrated in vacuo