Sodium Bicarbonate → HCID 58981690, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.06 g (15.0 mmol) of tert-butyl (1S,2S)-3-amino-2-hydroxy-1-methylpropylcarbamate & tert-butyl (1S,2R)-3-amino-2-hydroxy-1-methylpropylcarbamate in 100 mL of dichloromethane was added 3.78 g (45.0 mmol) of sodium bicarbonate and 50 mL of water. The reaction mixture was cooled to 0° C. and 16.5 mL (16.5 mmol) of a 1.0 M solution of 2-pyridinesulfonyl chloride in dichloromethane was added gradually over 20 min. The reaction mixture was stirred at room temperature for 16 h. The layers were then separated and the organic layer was dried over anhydrous magnesium sulfate, and concentrated under vacuum to afford the crude product. This product was purified via silica gel chromatography eluting with ethyl acetate:hexane (8:2) to afford 2.0 g (34%) of tert-butyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & tert-butyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ 8.72 (m, 1H), 8.07–7.92 (m, 2H), 7.51 (m, 1H), 6.25, 6.08 (2br s, 1H), 4.83-4.64 (m, 2H), 3.74–3.47 (m, 3H), 3.27–3.19 (m, 1H), 1.23, 1.22 (2s, 9H), 1.12 (m, 3H).

Provenance & Evidence