Triethylamine → HCID 15546709, Verbindung

HRID 854251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854251
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:18])[N:15]=[C:16](Cl)[C:11]=2[CH:10]=[CH:9]1)[CH3:2].[C:20]([O:24][C:25](=[O:40])[C@@H:26]([NH:29][C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[CH2:27][NH2:28])([CH3:23])([CH3:22])[CH3:21].C(N(CC)CC)C>CN1CCCC1=O>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[N:13]=[C:14]([CH3:18])[N:15]=[C:16]([NH:28][CH2:27][C@H:26]([NH:29][C:30]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[O:31])[C:25]([O:24][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:40])[C:11]=2[CH:10]=[CH:9]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10803731(S)-tert-Butyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoateHCID 15546708HCID 15546708, Verbindung

Produkt 1

HCID 15546709HCID 15546709, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1000 mg (3.5 mmol) of 4-(4-chloro-2-methyl-pyrrolo[2,3-d]pyrimidin-7-yl)-butyric acid ethyl ester (example 2a) in 7 ml N-methylpyrrolidone were added 1590 mg (5.4 mmol) of (2S)-3-amino-2-benzyloxycarbonylamino-propionic acid tert-butyl ester and 5.9 ml triethylamine and the reaction was stirred at 100° C. for 36 h. The reaction was diluted with 85 ml EE and extracted with water, aqueous citric acid and again with water. The organic phase was dried over MgSO4 filtered and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluting with DCM/EE (2:1). Yield: 719 mg.

Aufarbeitung

  1. additionThe reaction was diluted with 85 ml EE
  2. extractionextracted with water, aqueous citric acid and again with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica gel eluting with DCM/EE (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-c0bcfb06b0a449fe808f26514394499a
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259159B2

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