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Diisopropylethylamine → 4-[6-((2S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-purin-9-yl]-butyric acid ethyl ester

HRID 854247
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 854247
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2Cl)[CH3:2].C(N(CC)C(C)C)(C)C.[C:28]([O:32][C:33](=[O:48])[C@@H:34]([NH:37][C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH2:35][NH2:36])([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH:36][CH2:35][C@H:34]([NH:37][C:38]([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39])[C:33]([O:32][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:48])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoateHCID 155472644-(6-Chloro-purin-9-yl)-butyric acid ethyl ester

Produkt 1

HCID 155472654-[6-((2S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylamino)-purin-9-yl]-butyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1 g (3.72 mmol) of 4-(6-chloro-purin-9-yl)-butyric acid ethyl ester was dissolved in dimethylformamide (3 ml) and 2.6 ml (14.9 mmol) of N,N-diisopropylethylamine was added. 1.09 g (3.72 mmol) of (2S)-3-amino-2-benzyloxycarbonylamino-propionic acid tert-butyl ester and dimethylformamide (2 ml) were added. The reaction was stirred at 80° C. for 2 days. The solvent was removed in vacuo, the residue was dissolved in dichloromethane and the solution was washed three times with 10% aqueous citric acid solution and three times with water. The organic phase was dried with sodium sulfate, filtered and the solvent was removed in vacuo. Residual amounts of 4-(6-chloro-purin-9-yl)-butyric acid ethyl ester were removed as follows: the residue was dissolved in tetrahydrofuran and 2 g of a macroporous aminomethyl polystyrene resin was added. The suspension was heated at 60° C. for 5 hours, then stirred gently at room temperature for 16 hours. The resin was filtered off, washed with tetrahydrofuran, and the combined organic phase was dried in vacuo. Yield: 908 mg.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washthe solution was washed three times with 10% aqueous citric acid solution and three times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customResidual amounts of 4-(6-chloro-purin-9-yl)-butyric acid ethyl ester were removed
  8. dissolutionthe residue was dissolved in tetrahydrofuran
  9. addition2 g of a macroporous aminomethyl polystyrene resin was added
  10. temperatureThe suspension was heated at 60° C. for 5 hours
  11. stirringstirred gently at room temperature for 16 hours
  12. filtrationThe resin was filtered off
  13. washwashed with tetrahydrofuran
  14. customthe combined organic phase was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7b468c637b0a47fc95c924a592f0b934
Quelldatensatz
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07259159B2

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