반응 #640536

반응 방정식

N-4-methoxybenzyloxycarbonyl α-methyl β-alanine methyl ester

lithium hydroxide

→

N-4-Methoxybenzyloxycarbonyl α-methyl β-alanine

수율 97.3%

용매

methanol

반응 조건

후처리

1. 1
   농축The solution was concentrated in vacuo
2. 2
   workup.ADDITIONthe residue taken up in a mixture of water and ether
3. 3
   기타the phases separated
4. 4
   추출extracted three times with ether
5. 5
   세척The combined ethereal phase was washed with saturated aqueous sodium chloride solution
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   여과filtered
8. 8
   농축concentrated in vacuo

실험 절차

A solution of N-4-methoxybenzyloxycarbonyl α-methyl β-alanine methyl ester (2.81 g, 10.0 mmol) in 30 mL of 25% aqueous methanol was treated with lithium hydroxide (1.3 equivalents) at room temperature for a period of 2 h. The solution was concentrated in vacuo and the residue taken up in a mixture of water and ether and the phases separated and the organic phase discarded. The aqueous phase was acidified with aqueous potassium hydrogen sulfate to pH=1.5 and then extracted three times with ether. The combined ethereal phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 2.60 g, 97% of N-4-Methoxybenzyloxycarbonyl α-methyl β-alanine (N-Moz-AMBA) which was purified by recrystallization from a mixture of ethyl acetate and hexane to give 2.44 g, 91% of pure product, mp 96-97° C., MH+=268. 1H NMR (D6-acetone/300 MHz) 1.16 (3H, d, J=7.2Hz), 2.70 (1H, m), 3.31 (2H, m), 3.31 (3H, s), 4.99 (2H, s), 6.92 (2H, 4, J=8.7 Hz), 7.13 (2H, d, J=8.7 Hz).

출처