4-Methylmorpholine → 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid

HRID 1590812Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590812
ClC(OCC(C)C)=O.[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([OH:34])=O)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN1CCOCC1.[CH3:45][C:46]1[C:51]([C:52]([OH:54])=[O:53])=[C:50]([NH:55][C:56](=[O:62])[C@H:57]([CH:59]([CH3:61])[CH3:60])[NH2:58])[CH:49]=[CH:48][CH:47]=1>CN(C)C=O.O1CCCC1>[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:28]([N:30]1[CH2:37][CH2:36][CH2:35][C@H:31]1[C:32]([NH:58][C@H:57]([C:56]([NH:55][C:50]1[CH:49]=[CH:48][CH:47]=[C:46]([CH3:45])[C:51]=1[C:52]([OH:54])=[O:53])=[O:62])[CH:59]([CH3:61])[CH3:60])=[O:34])=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 11899094Z-Phe-pro-OHHCID 541805686-methyl-2-(L-valylamino)benzoic acid

Produkt 1

HCID 543276212-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acidAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Isobutyl chloroformate (0.17 ml) was added to a tetrahydrofuran solution (3.5 ml) containing N-benzyloxycarbonyl-L-phenylalanyl-L-proline (523 mg) and N-methylmorpholine (0.15 ml) at -15° C., and the mixture was stirred for 0.5 hour. An N,N-dimethylformamide solution (5.5 ml) containing 6-methyl-2-(L-valylamino)benzoic acid (220 mg) and N-methylmorpholine (0.12 ml) was added dropwise to the obtained reaction mixture at -15° C., and the mixture was stirred at this temperature for 0.5 hour and then at room temperature for two hours. The reaction mixture was treated by the same procedures as in item (c) of Example 1 to obtain 2-(N-benzyloxycarbonyl-L-phenylalanyl-L-prolyl-L-valyl)amino-6-methylbenzoic acid (317 mg).

Aufarbeitung

  1. additionwas added dropwise to the obtained reaction mixture at -15° C.
  2. stirringthe mixture was stirred at this temperature for 0.5 hour
  3. waitat room temperature for two hours

Quellen und Nachweise

ORD-Eintrag
ord-8a80297e57d64c4a89ee6570486caeb2
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204462

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