Z-Dap-OH → HCID 89813055, compound

Participants

Reaction Steps

To mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (200 mg, 0.63 mmol) and 3-amino-2-(S)-benzyloxycarbonylamino-propionic acid (745 mg, 3.12 mmol) (Bachem) in 2-methoxyethanol (10 mL) was added NaOMe solid (135 mg, 2.5 mmol). The resultant mixture was refluxed overnight. Reaction mixture was concentrated. Residue was dissolved in water (100 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried. It was purified by silica gel chromatography, eluting with 10-100% EtOAc (with 0.075% acetic acid)/CH2Cl2 (with 0.01% acetic acid) to provide the title compound 91 mg (0.17 mmol) in 28% yield. LC-MS ESI−: 525.05 (M−1)−.

Provenance & Evidence