trans-3-Amino-4-(2-methylpropyl)-2-azetidinone → butoxycarbonyl-D,L-lysyl-L-proline

HRID 2418445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2418445
C(O[C:9](=[O:24])[CH:10]([CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[NH:11][C:12]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:13])C1C=CC=CC=1.[NH2:25][C@H:26]1[C@H:29]([CH2:30][CH:31](C)C)N[C:27]1=[O:34].C(=NC(CCC)C(=O)C(OOCCCC)=O)=[O:36]>>[CH2:15]([O:14][C:12]([NH:11][CH:10]([C:9]([N:25]1[CH2:31][CH2:30][CH2:29][C@H:26]1[C:27]([OH:34])=[O:36])=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])=[O:13])[CH2:16][CH2:17][CH3:18]

Komponenten

4

Edukt 3

HCID 70056984trans-3-Amino-4-(2-methylpropyl)-2-azetidinoneHCID 77861463butoxycarbonyl-D,L-lysine benzyl esterHCID 131712975HCID 131712975, Verbindung

Produkt 1

HCID 131712974butoxycarbonyl-D,L-lysyl-L-proline

Versuchsvorschrift

N-α-[4-(2-methylpropyl)-2-oxo-3-azetidinyl]-N-ε-3°-butoxycarbonyl-D,L-lysine benzyl ester can be prepared from trans-3-amino-4-(2-methylpropyl)-2-azetidinone (Example 78) and benzyl ε-3°-butoxy carbonylamino-2-oxohexanoate. The benzyl group can be removed by hydrogenation and the product coupled with L-proline benzyl ester. The product, N-α-[4-(2-methylpropyl)-2-oxo-3-azetidinyl]-N-ε-3°-butoxycarbonyl-D,L-lysyl-L-proline benzyl ester, can then be debenzylated with hydrogen and the β-lactam hydrolyzed with dilute base to obtain N-α-(2-amino-1-carboxy-4-methylpentyl)-N-ε-3°-butoxycarbonyl-D,L-lysyl-L-proline. After benzoylation with benzoyl chloride in organic solvent, the t-Boc protecting group can be removed with trifluoroacetic acid so that one can obtain N-α-(2-benzamido-1-carboxy-4-methylpentyl)-D,L-lysyl-L-proline.

Aufarbeitung

  1. customThe benzyl group can be removed by hydrogenation
  2. additionwith dilute base

Quellen und Nachweise

ORD-Eintrag
ord-e60f1a2d86514a24a872f4aaa4e5ab5d
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04472380

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