(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidine → HCID 10266316, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 7C (32.4 mg) and (3S)-3-(tert-butoxycarbonylamino)pyrrolidine (55.8 mg) in acetonitrile (1 mL) in a sealed vial was heated for 24 hours then cooled and concentrated. The concentrate was dissolved in 1:1 DMSO/methanol (1 mL) and chromatographed by reverse phase HPLC. The product was suspended in 2-propanol (1 mL), treated with 1M LiOH (1.2 mL), heated at 80° C. for 18 hours in a sealed vial for 24 hours, and concentrated. The concentrate was treated with 10% citric acid to pH 4-6 and filtered. The filtrant was dissolved in 4M HCl/dioxane (1.5 mL), and this solution was stirred for 2 hours and concentrated. NMR (500 MHz DMSO-d6) δ 13.4 (m, 1H), 8.50 (m, 1H), 8.45 (s, 2H), 8.00 (m, 1H), 4.00-3.40 (m, 5H), 2.38 (m, 1H), 2.18 (m, 1H).

Provenance & Evidence