Diisopropylethylamine → HCID 70149057, compound

Participants

Reaction Steps

To (R)-N-(tert-butoxycarbonyl)alanine (220 mg, 1.16 mmol) in dry CH2Cl2 (2 mL) under argon were added PYBOP (604 mg, 1.16 mmol), 1-amino-7-(tert-butyldiphenylsilyloxy)naphthalene hydrochloride, as described above in Step C, (250 mg, 0.58 mmol), and N,N-diisopropylethylamine (0.40 mL, 2.3 mmol). The reaction mixture was stirred for 3 hrs, then partitioned between CH2Cl2 (250 mL) and 10% aqueous citric acid (75 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with CH2Cl2-20% ethyl acetate to yield the desired product as a white foam.

Provenance & Evidence