Diisopropylethylamine → HCID 178446030, Verbindung

HRID 1953998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1953998
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C:17]1[CH:25]=[CH:24][C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=1)=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[NH:26](C(OC(C)(C)C)=O)[C@@H:27]([C:32](O)=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:26][C@@H:27]([C:32]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([NH:16][C:17]1[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[CH:24][CH:25]=1)=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 637604tert-Butoxycarbonyl-D-leucineHCID 178512898HCID 178512898, Verbindung

Produkt 1

HCID 178446030HCID 178446030, VerbindungAusbeute 107,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Following the procedures of Preparation Ic, a reaction mixture comprising (i) 910 mg (1.57 mmol) of H-Gly-L-Arg-pNA.2H-TFA, (ii) 363 mg (1.57 mmol) of Boc-D-Leu-OH, (iii) 1.2 ml of DIEA and (iv) 695 mg (1.57 mmol) of Bop is reacted in DMF and the reaction mixture is kept at RT for 2 h, with stirring. After evaporation to dryness under vacuum, the evaporation residue is chromatographed on silica gel using a CHCl3 /MeOH/AcOH gradient (20/3/1 to 10/3/1 v/v) as the eluent. The homogeneous fractions collected are pooled and the eluent is evaporated off. Lyophilization gives 785 mg (yield: 80%) of the expected product in pure form.

Aufarbeitung

  1. customthe procedures of Preparation Ic
  2. customAfter evaporation to dryness under vacuum
  3. customthe evaporation residue is chromatographed on silica gel using a CHCl3 /MeOH/AcOH gradient (20/3/1 to 10/3/1 v/v) as the eluent
  4. customThe homogeneous fractions collected
  5. customthe eluent is evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-e28d666b98df4df8a6933d64aa002408
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121239

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