Reaktion #67349

ord-9478de3ba77c4b84b1e4606317a79b28

Reaktionsgleichung

CC(C)OC(=O)N1Cc2cc(O)c([N+](=O)[O-])cc2C[C@H]1C(=O)O
(S)-7-Hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester
COC(=O)[C@@H](N)Cc1ccc(-c2ccc(C#N)cc2)cc1.Cl
(S)-2-amino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester-hydrochloride
→
COC(=O)[C@H](Cc1ccc(-c2ccc(C#N)cc2)cc1)NC(=O)[C@@H]1Cc2cc([N+](=O)[O-])c(O)cc2CN1C(=O)OC(C)C
amide
Ausbeute 79.7%
COC(=O)[C@H](Cc1ccc(-c2ccc(C#N)cc2)cc1)NC(=O)[C@@H]1Cc2cc([N+](=O)[O-])c(O)cc2CN1C(=O)OC(C)C
(S)-3-[(S)-2-(4′-Cyano-biphenyl-4-yl)-1-methoxycarbonyl-ethylcarbamoyl]-7-hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid isopropyl ester
Ausbeute 79.7%

Edukte

CC(C)OC(=O)N1Cc2cc(O)c([N+](=O)[O-])cc2C[C@H]1C(=O)O
(S)-7-Hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester
COC(=O)[C@@H](N)Cc1ccc(-c2ccc(C#N)cc2)cc1.Cl
(S)-2-amino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester-hydrochloride

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

(S)-7-Hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester 3-methyl ester (2.4 mmol) was hydrolyzed according to general procedure B to provide the acid (0.704 g). (S)-7-Hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester (2.16 mmol) was coupled with (S)-2-amino-3-(4′-cyano-biphenyl-4-yl)-propionic acid methyl ester-hydrochloride (2.38 mmol) according to general procedure A to provide the amide (1.01 g) LC/MS: m/z 588.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524708B2uspto-grants-2013_09