4-Methylmorpholine → 3-((S)-2-tertbutoxycarbonylaminopropionylamino)-6-fluoro-2-phenylaminobenzoic acid methyl ester

Participants

Reaction Steps

A mixture of 3-amino-6-fluoro-2-phenylaminobenzoic acid methyl ester (2.0 g, 7.7 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (1.6 g, 8.45 mmol), HOAt (760 mg, 8.45 mmol), 4-methylmorpholine (1.86 mL, 16.9 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.07 g, 8.45 mmol) in DCM (20 mL) was stirred at RT for 2 h. The reaction mixture was then partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in cyclohexane) to afford 3-((S)-2-tertbutoxycarbonylaminopropionylamino)-6-fluoro-2-phenylaminobenzoic acid methyl ester. LCMS (Method B): RT 3.65 min [M+H]+ 432.3.

Provenance & Evidence