Tert-butoxycarbonylalanine → HCID 70205253, compound

Participants

Reaction Steps

To a solution of 1,3-dicyclohexylcarboimide (483 mg, 2.15 mmol) and 1-hydroxybenzotriazolehydrate (291 mg 2.15 mmol) in 10 m of tetrahydrofuran were added N-(t-butoxycarbonyl)-L-alanine (352 mg, 1.86 mmol) and 4-dimethylaminopyridine (50 mg, 0.41 mmol) in order. The reaction mixture was stirred at room temperature for 5 min. Then, (S)-(+)-4-phenyl-1-[N-(4-aminobenzoyl)-indoline-5 -sulfonyl]-4,5-dihydro-2-imidazolone (200 mg, 0.41 mmol) prepared in Example 65 was added thereto and the whole mixture was stirred at room temperature for 24 hours. After stirring, the reaction mixture was filtered. The filtrate was diluted with ethylacetate, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The crude product thus obtained was purified by silica gel column chromatography (eluent: ethylacetate/hexane=2/1, v/v) to provide 260 mg (Yield: 96%) of (S)-(+)-4-phenyl-1-[N-{4-(2-t-butoxycarbonylaminopropanoyl)-aminobenzoyl}indoline-5-sulfonyl]-4,5-dihydro-2-imidazolone.

Provenance & Evidence