تفاعل #324478

معادلة التفاعل

NaHCO3

azetidine-1,3-dicarboxylic acid mono-tert-butyl ester

O,N-dimethyl-hydroxylamine hydrochloride

triethylamine

HATU

→

title compound

المردود 84.3%

3-(Methoxy-methyl-carbamoyl)-azetidine-1-carboxylic acid tert-butyl ester

المردود 84.3%

المذيبات

ethyl acetate

DMF

DCM

ظروف التفاعل

المعالجة

1. 1
   استخلاصThe aqueous portion was extracted three times with ethyl acetate
2. 2
   تجفيفThe combined organic fractions were dried (Na2SO4)
3. 3
   تركيزconcentrated
4. 4
   أخرىthe crude product was purified

الإجراء التجريبي

To a solution of azetidine-1,3-dicarboxylic acid mono-tert-butyl ester (3.5 g, 17 mmol) in DMF (50 mL) was added O,N-dimethyl-hydroxylamine hydrochloride (3.4 g, 34 mmol), triethylamine (9.6 mL, 69 mmol), HATU (13.4 g, 34.6 mmol) and DCM (125 mL). After stirring for 16 h, saturated NaHCO3 solution and ethyl acetate were added. The aqueous portion was extracted three times with ethyl acetate. The combined organic fractions were dried (Na2SO4) and concentrated and the crude product was purified using RP HPLC (basic conditions) to provide the title compound (3.5 g, 83%) MS (ESI): mass calcd. for C11H20N2O4, 244.1; m/z found, 189.1 [M-t-Bu]+. 1H NMR (CDCl3): 4.14-4.03 (m, 2H), 4.05 (t, J=8.7 Hz, 2H), 3.66 (s, 3H), 3.63-3.59 (m, 1H), 3.21 (s, 1H), 1.43 (s, 9H).

المصدر