تفاعل #356785

معادلة التفاعل

2(S)-tert-butoxycarbonylaminosuccinic acid 1-benzyl ester

1,1′-carbonyldiimidazole

hydrochloric acid

nitromethane

potassium tert-butoxide

→

Benzyl 2(S)-tert-butoxycarbonylamino-5-nitro-4-oxopentanoate

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent is evaporated
2. 2
   أخرىAfter separation of the phases
3. 3
   استخلاصthe organic phase is extracted twice with water
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated
6. 6
   أخرى13 g (99% of theory) of product are obtained

الإجراء التجريبي

A solution A of 10 g (30.9 mmol) of 2(S)-tert-butoxycarbonylaminosuccinic acid 1-benzyl ester and 5.27 g (32.5 mmol) of 1,1′-carbonyldiimidazole in 100 ml of tetrahydrofuran is stirred at RT for 5 h. 18.8 g (30.9 mmol) of nitromethane are added dropwise to a solution B of 3.2 g (34.2 mmol) of potassium tert-butoxide in 100 ml of tetrahydrofuran at 0° C. Solution B is stirred while warming to RT, and then solution A is added dropwise at RT. The resulting mixture is stirred at RT for 16 h and adjusted to pH 2 using 20% hydrochloric acid. The solvent is evaporated. The remaining crude product is taken up in ethyl acetate/water. After separation of the phases, the organic phase is extracted twice with water, dried over sodium sulfate and concentrated. 13 g (99% of theory) of product are obtained.

المصدر