Hydrochloric Acid → (3S)-3-amino-7-{[(dimethylamino)sulfonyl]amino}-2-hydroxy-N-(3-pyridinylmethyl)heptanamide dihydrochloride

Participants

Reaction Steps

A 0° C. solution of 1.13 g (2.4 mmol) of tert-butyl (1S)-5-{[(dimethylamino)sulfonyl]amino}-1-{1-hydroxy-2-oxo-2-[(3-pyridinylmethyl)amino]ethyl}pentylcarbamate in 100 mL of ethyl acetate was bubbled with hydrogen chloride gas for 5 min and stirred at room temperature for 30 min before being concentrated under reduced pressure to afford 1.06 g (>99%) of (3S)-3-amino-7-{[(dimethylamino)sulfonyl]amino}-2-hydroxy-N-(3-pyridinylmethyl)heptanamide dihydrochloride. 1H NMR (300 MHz, DMSO-d6) δ 8.92 (t, J=6 Hz, 1H), 8.76 (m, 2H), 8.09 (bs, 1H), 7.87 (m, 2H), 7.17 (m, 1H), 6.68 (m, 1H), 4.46 (m, 2H), (4.32 (d, J=3 Hz) and 4.18 (d, J=3 Hz), 1H), 3.37 (m, 1H), 2.83 (m, 2H), 2.67 (s, 6H), 1.25-1.60 (m, 6H). ES-LCMS m/z 374 (M+H).

Provenance & Evidence