反応 #50799

反応方程式

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

methylsulfide

→

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

反応条件

後処理

1. 1
   その他sparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists
2. 2
   その他Sparge with nitrogen for 10 minutes at -78° C.
3. 3
   その他to remove excess ozone
4. 4
   温度to warm to room temperature
5. 5
   その他evaporate the solvent in vacuo
6. 6
   workup.DISSOLUTIONdissolve the residue in ethyl acetate (200 mL)
7. 7
   洗浄Wash with water, saturated sodium chloride
8. 8
   乾燥dry (Mg SO4)
9. 9
   その他evaporate the solvent in vacuo

実験手順

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).

出典