反应 #49967

反应方程式

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

methyl sulfide

→

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

反应条件

后处理

1. 1
   其他sparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists
2. 2
   其他Sparge with nitrogen for 10 minutes at -78° C.
3. 3
   其他to remove excess ozone
4. 4
   温度to warm to room temperature
5. 5
   其他evaporate the solvent in vacuo
6. 6
   workup.DISSOLUTIONdissolve the residue in ethyl acetate (200 mL)
7. 7
   洗涤Wash with water, saturated sodium chloride
8. 8
   干燥dry (MgSO4)
9. 9
   其他evaporate the solvent in vacuo

实验过程

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 methyl sulfide (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 (MgSO4) 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).

来源