HCID 11279346, compound → HCID 86755666, compound

Participants

Reaction Steps

A solution of (1S,2R,5R,6S)-2-Azido-3-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (IX) (974 mg, 2.84 mmol) in thioacetic acid (6.5 mL) was stirred at 70° C. for 2 d. The reaction mixture was concentrated in vacuum and subjected to silica gel column chromatography with hexane/ethyl acetate 3:2->1:1 to yield (1S,2R,5R,6S)-2-acetylamino-3-oxo-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XVI) (726 mg, 71%) as a pink oil. 1H-NMR (250 MHz, CDCl3) □1.25 (3H, t, 1=7.1 Hz), 1.63 (1H, t, J=3.5 Hz), 2.05 (3H, s), 2.32 (1H, ddd,J=7, 6,3.5 Hz), 2.54 (1H, d,J=19 Hz), 2.90 (1H, dd,J=19, 6 Hz), 3.06 (1H, dd, J=7, 3.5 Hz), 4.12 (2H, m), 5.16 (1H, d, J=12 Hz), 5.25 (1H, d, J=12 Hz), 7.24-7.35 (5H, m); MS[ISP] 360 (M+H+); □D20 +44.33° (c=0.97, CHCl3).

Provenance & Evidence