Sodium Hydroxide → 1,1-Dimethylethyl N-[(1S,2S,4S)-4-amino-2-hydroxy-5-phenyl-1-(phenylmethyl)pentyl]carbamate

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Reaction Steps

(2S,3S,5S)-2-tert-Butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane oxalate (500 mg, 1.05 mmol) obtained in Example 43 (A) was suspended in toluene (5 ml). An aqueous solution (5 ml) of NaOH (200 mg) was added thereto and the mixture was vigorously stirred, then separated. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated to give the desired compound as colorless crystals. Yield: 340 mg (84%). 1H NMR(500 MHz, CDCl3) δ ppm 7.29-7.06(m, 10H), 5.08(d, 1H, J=9.5 Hz), 3.77(d, 1H, J=10.1 Hz), 3.65(broad q, 1H), 3.01 (m, 1H), 2.86(d, 2H, J=8.0 Hz), 2.77(dd, 1 H, J=1 3.6, 4.6 Hz), 2.40(dd, 1H, J=13.6, 8.5 Hz), 1.55-1.39(m 2H), 1.42(s, 9H).

Provenance & Evidence