4-Methylmorpholine → (S)-2-{(S)-3,3-Dimethyl-2-[(1-methyl-piperidine-4-carbonyl)-amino]-butyrylamino}-propionic acid ethyl ester

HRID 44141

Reaktionsgleichung

Reaktionsgleichung von HRID 44141
[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([NH:7][C:8](=[O:15])[C@@H:9]([NH2:14])[C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6])[CH3:2].[CH3:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24](O)=[O:25])[CH2:20][CH2:19]1.C(OC(Cl)=O)C(C)C.CN1CCOCC1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[C@@H:5]([NH:7][C:8](=[O:15])[C@@H:9]([NH:14][C:24]([CH:21]1[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]1)=[O:25])[C:10]([CH3:11])([CH3:13])[CH3:12])[CH3:6])[CH3:2]

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 27369391-Methylpiperidine-4-carboxylic acidHCID 86674878(S)-2-((S)-2-Amino-3,3-dimethyl-butyrylamino)-propionic acid ethyl ester

Produkt 1

HCID 67325020(S)-2-{(S)-3,3-Dimethyl-2-[(1-methyl-piperidine-4-carbonyl)-amino]-butyrylamino}-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

For compound (A48) (S)-2-((S)-2-Amino-3,3-dimethyl-butyrylamino)-propionic acid ethyl ester was coupled with 1-Methyl-piperidine-4-carboxylic acid using isobutylchloroformate and N-methylmorpholine in DMF to give (S)-2-{(S)-3,3-Dimethyl-2-[(1-methyl-piperidine-4-carbonyl)-amino]-butyrylamino}-propionic acid ethyl ester. This was then quaternised with MeI in DCM-acetone and subsequently hydrolysed using an hydroxide resin such as Ambersep 900-OH resin.

Quellen und Nachweise

ORD-Eintrag
ord-94ce4938ec99444bb640482c7e136ef9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541363B2

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