تفاعل #571859

معادلة التفاعل

N2 [[(phenylmethyl)oxy]carbonyl]-N-[2-[[[(phenylmethyl)oxy]carbonyl]amino]-3-methoxy-3-oxopropoxy]-L-serinamide

triphenylphosphine

undecan-7-ene

diethylazodicarboxylate

→

(3S)-1-Hydroxy-3-[[[(phenylmethyl)oxy]carbonyl]-amino]-2-azetidinone

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىtetrahydrofuran is removed by evaporation
2. 2
   أخرىthe resulting residue is partitioned between ethyl acetate and saturated sodium bicarbonate
3. 3
   غسيلThe aqueous layer is washed once with ethyl acetate
4. 4
   استخلاصextracted with ethyl acetate (five times)
5. 5
   أخرىThe combined extracts are dried
6. 6
   تركيزconcentrated to a crystalline solid (1.8 g)
7. 7
   أخرىA portion is recrystallized from acetone/hexane (two times)
8. 8
   أخرىto give an analytical sample, melting point 128°-131° C.

الإجراء التجريبي

To a cold (0°-5° C.) solution of N2 -[[(phenylmethyl)oxy]carbonyl]-N-[2-[[[(phenylmethyl)oxy]carbonyl]amino]-3-methoxy-3-oxopropoxy]-L-serinamide (6.08 g) in distilled tetrahydrofuran (100 ml) is added triphenylphosphine (3.6 g) followed by diethylazodicarboxylate (2.15 ml, 2.38 g). The reaction mixture is allowed to stir for twelve hours under nitrogen, whereupon 7.0 ml of 1,8-diazabicyclo[5.4.0.]undecan-7-ene is added. After 30 minutes, tetrahydrofuran is removed by evaporation and the resulting residue is partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer is washed once with ethyl acetate, then adjusted to pH 2 with saturated potassium bisulfate, and extracted with ethyl acetate (five times). The combined extracts are dried and concentrated to a crystalline solid (1.8 g). A portion is recrystallized from acetone/hexane (two times) to give an analytical sample, melting point 128°-131° C.

المصدر