Ethyl oxoacetate → N-[N2-(1(S)-carboxy-3-phenylpropyl)-N6-ethoxycarbonylmethyl-L-lysyl]-L-proline

HRID 1583935

Reaktionsgleichung

[C:1]([C@@H:4]([NH:13][C@H:14]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([OH:3])=[O:2].[C:30]([O:34][CH2:35][CH3:36])(=[O:33])[CH:31]=O>>[C:1]([C@@H:4]([NH:13][C@H:14]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24]([OH:26])=[O:25])=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:31][C:30]([O:34][CH2:35][CH3:36])=[O:33])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:3])=[O:2]

Komponenten

Edukt 2

HCID 70211Ethyl oxoacetate

HCID 5362119Lisinopril

Produkt 1

HCID 54237465N-[N2-(1(S)-carboxy-3-phenylpropyl)-N6-ethoxycarbonylmethyl-L-lysyl]-L-proline

Versuchsvorschrift

The reductive alkylation of N-[N2 (1(S)-carboxy-3-phenylpropyl)-L-lysyl]-L-proline and ethyl glyoxylate was carried out in accordance with the procedures described in Example 1 to give N-[N2 -(1(S)-carboxy-3-phenylpropyl)-N6 -ethoxycarbonylmethyl-L-lysyl]-L-proline. The product was then treated with ammonia at 100° C. followed by absorption on strong acid ion exchange resin and eluting with 2% pyridine in water. Freeze drying of product-rich cuts afforded N-[N2 -(1(S)-carboxy-3-phenylpropyl)-N6 -carbamoylmethyl-L-lysyl]-L-proline. The nmr spectrum was consistent with the structure.

Quellen und Nachweise

ORD-Eintrag: ord-b5adf0282dfe48d299e223be09a8cca6
Quelldatensatz: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04555503

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