4-Methylmorpholine → t-butyloxycarbonyl-L-leucyl-L-prolinamide

HRID 248815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 248815
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([NH2:23])=[O:22])=[O:18])[CH2:10][C:11]1[CH:16]=CC=C[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N[C@H](C(O)=O)CC(C)C)=O)(C)(C)C.CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.N1CCC[C@H]1C(N)=O>O1CCCC1.CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([NH2:23])=[O:22])=[O:18])[CH2:10][CH:11]([CH3:16])[CH3:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Komponenten

8

Edukt 5

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 12707183(S)-Pyrrolidine-2-carboxamide monohydrochlorideHCID 13576349Boc-L-Phe-L-Pro-NH2

Produkt 1

HCID 7031925t-butyloxycarbonyl-L-leucyl-L-prolinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Following the general procedure described previously for t-butyloxycarbonyl-L-phenylalanyl-L-prolinamide, a solution of t-butyloxycarbonyl-L-leucine (32.64 g), in tetrahydrofuran was activated by treatment with N-methylmorpholine (18.22 ml), followed by isobutylchloroformate (16.99 ml) at -5° C. After 15 minutes, L-prolinamide hydrochloride (15.0 g) was added as a solution in dimethylformamide, followed by N-methylmorpholine (18.22 ml) and the mixture stirred overnight at room temperature. The reaction was worked up as described previously to give the desired product, which was used for the next step without further purification.

Quellen und Nachweise

ORD-Eintrag
ord-dab328d83a3549958a7c86af4668c86e
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212158

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