Water → HCID 67224085, Verbindung

HRID 1963976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963976
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C.[Br:58][C:59]1[CH:68]=[CH:67][C:62]([C:63](=[N:65]O)[NH2:64])=[CH:61][CH:60]=1>CN(C)C=O>[Br:58][C:59]1[CH:68]=[CH:67][C:62]([C:63]2[N:65]=[C:10]([C@@H:9]3[CH2:13][CH2:14][CH2:15][N:8]3[C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[O:12][N:64]=2)=[CH:61][CH:60]=1

Komponenten

8

Edukt 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27568384-Bromo-N-hydroxybenzimidamide

Produkt 1

HCID 67224085HCID 67224085, VerbindungAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-L-proline (2.5 g, 11.6 mmol) in N,N-dimethylformamide (18 mL), O-(Benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (TBTU, 3.73 g, 11.6 mmol), HOBt.H2O (0.36 g, 2.32 mmol) and DIPEA (10.2 ml, 58.1 mmol) were added. After the reaction mixture was stirred at room temperature for 5 minutes, 4-Bromo-N′-hydroxybenzimidamide 15 (2.5 g, 11.6 mmol) was added. The mixture was then stirred at 110° C. for 2.5 hours. After cooled to room temperature, the resulting mixture was extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated to yield a crude yellow liquid, which was purified with chromatography (ethyl acetate: n-hexane=1:10) to give the desired product 16a (2.5 g).

Aufarbeitung

  1. stirringThe mixture was then stirred at 110° C. for 2.5 hours
  2. temperatureAfter cooled to room temperature
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude yellow liquid, which
  8. customwas purified with chromatography (ethyl acetate: n-hexane=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-f8d418972cb8425887c7bd47c64c41f3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415482B2

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