반응 #50799

반응 방정식

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

반응 조건

후처리

1. 1
   기타sparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists
2. 2
   기타Sparge with nitrogen for 10 minutes at -78° C.
3. 3
   기타to remove excess ozone
4. 4
   온도to warm to room temperature
5. 5
   기타evaporate the solvent in vacuo
6. 6
   workup.DISSOLUTIONdissolve the residue in ethyl acetate (200 mL)
7. 7
   세척Wash with water, saturated sodium chloride
8. 8
   건조dry (Mg SO4)
9. 9
   기타evaporate the solvent in vacuo

실험 절차

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).

출처