Water → (S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

HRID 342896

反応式

HRID 342896 の反応式
C1(=O)N([NH:6][C@H:7]([C:15]([NH2:17])=[O:16])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)C(=O)C2=CC=CC=C12.[CH2:24]([CH2:28][CH:29]=O)[CH2:25][CH:26]=O.[OH2:31].[C:32]1([CH3:42])[CH:37]=[CH:36][C:35](S(O)(=O)=O)=[CH:34][CH:33]=1.[O:43]1[CH2:47]CCC1.ClCCl>ClCCl>[O:43]=[C:47]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:42](=[O:31])[N:6]1[C@@H:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]([N:17]1[CH:26]=[CH:25][CH2:24][CH:28]=[CH:29]1)=[O:16]

参加物

7

反応物 5

HCID 962WaterHCID 3485GlutaraldehydeHCID 6101p-Toluenesulfonic acidHCID 21919333Tetrahydrofurane dichloromethaneHCID 53840537phthalimido-(S)-phenyalanine amide

生成物 1

HCID 15380836(S)-N-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-3-phenylpropyl]-1,4-dihydro-pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Combine phthalimido-(S)-phenyalanine amide (3.0 g, 10 mmol) and a solution of glutaric dialdehyde (2.0 g, 50% by weight in water) in dichloromethane (200 mL). Heat to reflux with azeotropic removal of water from the refluxate. Add p-toluenesulfonic acid (60 mg). Continue heating at reflux. Pass the refluxate through oven dried 4 Å molecular sieves. After 4 days, cool the reaction mixture to ambient temperature. Extract with 5% sodium bicarbonate solution. Extract the 5% sodium bicarbonate solution with dichloromethane. Combine the organic layers and dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% tetrahydrofuran/dichloromethane to give the title compound.

後処理

  1. temperatureHeat
  2. temperatureContinue heating
  3. temperatureat reflux
  4. customPass the refluxate through oven dried 4 Å molecular sieves
  5. extractionExtract with 5% sodium bicarbonate solution
  6. extractionExtract the 5% sodium bicarbonate solution with dichloromethane
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

出典と根拠

ORDレコード
ord-84c3eb894d9f40a3a9fc5b2f015a416a
出典データセット
uspto-grants-1999_01
特許番号
US05859252

関連ノート

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