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

HRID 129439ノート

反応式

HRID 129439 の反応式
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]([NH:15][C@H:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17][O:18][CH2:19][CH:20]=C)=[O:14].CSC.C(Cl)Cl.C[OH:40]>>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:13]([NH:15][C@H:16]([C:22]([O:24][CH3:25])=[O:23])[CH2:17][O:18][CH2:19][CH:20]=[O:40])=[O:14]

参加物

4

反応物 3

HCID 1068Dimethyl SulfideHCID 21226129Dichloromethane methanolHCID 70044917N-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-O-2-propenyl-L-serine, methyl ester

生成物 1

HCID 131717895N-[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

温度
-78 °C

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 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).

後処理

  1. customsparge with a mixture of ozone/oxygen for approximately 10 minutes until a blue color persists
  2. customSparge with nitrogen for 10 minutes at -78° C.
  3. customto remove excess ozone
  4. temperatureto warm to room temperature
  5. customevaporate the solvent in vacuo
  6. dissolutiondissolve the residue in ethyl acetate (200 mL)
  7. washWash with water, saturated sodium chloride
  8. dry with materialdry (MgSO4)
  9. customevaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-8ffe6b190c744510bfd178b7055cd2ed
出典データセット
uspto-grants-1995_11
特許番号
US05468745

反応ノート

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