5-Aminovaleric acid → 5-{[4-Hydroxy-7-(4-methoxy-benzylamino)-isoquinoline-3-carbonyl]amino}-pentanoic acid

Reaktionsgleichung

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22](OC)=[O:23].[NH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+].CO>>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)=[CH:9][CH:10]=2)[CH:5]=[N:4][C:3]=1[C:22]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:23]

Komponenten

Edukt 4

HCID 1385-Aminovaleric acid

HCID 887Methanol

HCID 10942334Sodium Methoxide

HCID 89813034Methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate

Produkt 1

HCID 898129995-{[4-Hydroxy-7-(4-methoxy-benzylamino)-isoquinoline-3-carbonyl]amino}-pentanoic acid

Versuchsvorschrift

A mixture of methyl 4-hydroxy-7-(4-methoxybenzylamino)isoquinoline-3-carboxylate (21.0 mg, 0.06 mmol), 5-aminovaleric acid (269.3 mg, 2.3 mmol, Sigma-Aldrich) and NaOMe in MeOH (3.0 mL, 1.5 mmol, 0.5 M solution, Sigma-Aldrich) was heated to reflux for 20 hours before cooling to room temperature. The solvent was removed in vacuo and the residue was dissolved in H2O (10 mL) and EtOAc (10 mL). To the stirred mixture was added 1 N hydrochloric acid until pH was 1. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were dried over MgSO4, concentrated, and purified by flash chromatography (0-30% MeOH/CH2Cl2) to give the title compound in 14 mg. MS: (−) m/z 422.13 (M−1).