Sodium Hydroxide → HCID 11627558, compound

Participants

Reaction Steps

To 133 (2.36 g, 6.2 mmol) dissolved in THF (12 ml), was added a solution of N-(2-aminoethyl)carbamic acid tert-butyl ester (163a, 1 ml, 6.2 mmol) in THF (12 ml) followed by addition of 2.5N NaOH (2.5 ml, 6.2 mmol). The reaction mixture was allowed to reflux overnight under nitrogen. The reaction mixture was extracted 3 times with ethyl acetate; combined organic layers were washed with brine solution and dried over potassium carbonate. The filtered sample was concentrated on the rotary evaporator, and the resulting solid was dried overnight under vacuum. Chromatography [Biotage Horizon HPFC system, silica gel, gradient method 0 to 5% CH3OH in CH2Cl2 (over 600 mL)] yielding a white solid (E65, 2.54 mg, 81% yield), mp 94° C.; HPLC: Intertsil ODS-3V C18, 30:70 [(KH2PO4 (0.01M, pH 3.2): CH3CN], 264 nm, Rt 9.7 min, 99.8% purity; MS (TOF MS ES+), m/z 508 (36.5), 506 (M+H, 100).

Provenance & Evidence