تفاعل #310870

معادلة التفاعل

(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

→

(5R,6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate

المذيبات

benzene

ظروف التفاعل

المعالجة

1. 1
   أخرىis deoxygenated
2. 2
   أخرىby bubbling through nitrogen for 10 minutes
3. 3
   درجة الحرارةDuring heating the solid
4. 4
   درجة الحرارةThe mixture is then cooled
5. 5
   ترشيحfiltered
6. 6
   أخرىto remove the catalyst
7. 7
   تركيزthe filtrate is concentrated in vacuo

الإجراء التجريبي

A suspension of (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one (56.4 mg, 0.15 mmol) and rhodium (II) acetate (0.1 mg) in dry benzene (3 ml) is deoxygenated by bubbling through nitrogen for 10 minutes. The mixture is then heated to 78° C. for 1 hour. During heating the solid starting material gradually goes into solution. The mixture is then cooled, filtered to remove the catalyst, and the filtrate is concentrated in vacuo to yield (5R,6S) p-nitrobenzyl 6-[(R)-1-hydroxyethyl]-1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate, 51 mg. (98%) as a colorless oil which slowly crystallized at room temperature (22° C.).

المصدر