تفاعل #308385

معادلة التفاعل

1-Boc-azetidine-3-carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

EDC

HOBt

DIPEA

→

4

المردود 99.6%

tert-butyl 3-(methoxy(methyl)carbamoyl)azetidine-1-carboxylate

المردود 99.6%

المذيبات

water

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with EtOAc (2×100 mL)
2. 2
   غسيلThe combined organic extracts were washed with water (150 mL) and brine (150 mL)
3. 3
   تجفيفdried over MgSO4
4. 4
   تركيزconcentrated under vacuum

الإجراء التجريبي

To a solution of 1-Boc-azetidine-3-carboxylic acid (5.0 g, 24.9 mmol) in DMF (40 mL) was added N,O-dimethylhydroxylamine hydrochloride (2.89 g, 29.8 mmol), EDC (5.55 g, 29.8 mmol), HOBt (3.36 g, 24.9 mmol) and DIPEA (9.82 mL, 54.7 mmol). The reaction was stirred at room temperature for 20 h. The reaction was diluted with water (150 mL) and extracted with EtOAc (2×100 mL). The combined organic extracts were washed with water (150 mL) and brine (150 mL), dried over MgSO4 and concentrated under vacuum to afford 4 as a clear colorless oil (6.06 g, 99%); 1H-nmr (400 MHz, CDCl3) δ 4.21-4.11 (m, 2H), 4.05 (t, J=8.0 Hz, 2H), 3.66 (s, 3H), 3.68-3.59 (m, 1H), 3.21 (s, 3H), 1.44 (s, 9H); m/z 189.1 [M−tBu].

المصدر