Water → Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1383744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383744
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26].O.C(OCC)(=O)C>C1COCC1.ClC(OCC(C)C)=O.CN1CCOCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:41])[CH3:42])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Produkt 1

HCID 131722753Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 79724-MethylmorpholineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 62365Isobutyl chloroformateLösungsmittel

Versuchsvorschrift

To a solution of Z-Phe-OH (742 mg) in THF (3 ml), isobutyl chloroformate (0.32 ml) and NMM (0.27 ml) were added under cooling with ice and the mixture was stirred for 15 minutes. Subsequently, a solution of N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (600 mg) in THF (3 ml) was added and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture and extraction was effected with ethyl acetate. The extract was washed with saturated brine, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2) to give Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 611 mg (58%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 10 hours
  3. washThe extract was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2)

Quellen und Nachweise

ORD-Eintrag
ord-e8669919cca647fb9505c605464bfc23
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255285B1

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