تفاعل #50799

معادلة التفاعل

N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-propenyl-L-serine, methyl ester

methylene chloride methanol

methylsulfide

→

N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-oxoethyl-L-serine, methyl ester

ظروف التفاعل

المعالجة

1. 1
   أخرىsparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists
2. 2
   أخرىSparge with nitrogen for 10 minutes at -78° C.
3. 3
   أخرىto remove excess ozone
4. 4
   درجة الحرارةto warm to room temperature
5. 5
   أخرىevaporate the solvent in vacuo
6. 6
   workup.DISSOLUTIONdissolve the residue in ethyl acetate (200 mL)
7. 7
   غسيلWash with water, saturated sodium chloride
8. 8
   تجفيفdry (Mg SO4)
9. 9
   أخرىevaporate the solvent in vacuo

الإجراء التجريبي

Dissolve N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-propenyl-L-serine, methyl ester (13 g, 29.8 mmol ) in methylene chloride/methanol (10:1, 220 mL). Cool to -78° C. and sparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists. Sparge with nitrogen for 10 minutes at -78° C. to remove excess ozone. Treat with methylsulfide (60 mL, 0.82 mol) and allow to warm to room temperature. Stir at room temperature for 2.5 hours, evaporate the solvent in vacuo and dissolve the residue in ethyl acetate (200 mL). Wash with water, saturated sodium chloride, dry (Mg SO4) and evaporate the solvent in vacuo to give the intermediate N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-oxoethyl-L-serine, methyl ester as a foam (13.6 g).

المصدر