(S)-2-amino-3-(4'-cyano-biphenyl-4-yl)-propionic acid methyl ester hydrochloride → (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

HRID 13595

Reaction equation

HRID 13595 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C@H:16]([C:17](O)=[O:18])[CH2:15][C:14]2[C:9](=[CH:10][C:11]([OH:23])=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=2)[CH2:8]1)=[O:6])([CH3:3])[CH3:2].Cl.[CH3:25][O:26][C:27](=[O:45])[C@@H:28]([NH2:44])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=2)=[CH:32][CH:31]=1>>[CH:1]([O:4][C:5]([N:7]1[C@H:16]([C:17](=[O:18])[NH:44][C@H:28]([C:27]([O:26][CH3:25])=[O:45])[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=3)=[CH:34][CH:35]=2)[CH2:15][C:14]2[C:9](=[CH:10][C:11]([OH:23])=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=2)[CH2:8]1)=[O:6])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 66719258(S)-2-amino-3-(4'-cyano-biphenyl-4-yl)-propionic acid methyl ester hydrochlorideHCID 66922707(S)-7-Hydroxy-6-nitro-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-isopropyl ester

Product 1

HCID 66923127(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 esterYield 79.7%

Procedure

(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.

Sources & evidence

ORD record
ord-ec56c214830844d8a92f0fff4eeb5d48
Source dataset
uspto-grants-2010_06
Patent number
US07727983B2

Linked notes

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