Dimethyl Sulfoxide → HCID 57013824, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII) (845 mg, 2.45 mmol) in THF (21 mL) and H2O (6 mL) was added LiOH.H2O (411 mg, 9.8 mmol) and the mixture was stirred at 23° C. for 18 h. The benzyl alcohol was extracted with ether, the aqueous layer acidified with 1 M KHSO4 -sol., saturated with solid NaCl, extracted with EtOAc (4×50 mL) and dried over MgSO4. After removal of the solvent under vacuum crude (1S,2R,3R,5R,6S)-2-azido-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid (XI) (581 mg, quant.) was obtained as white solid, sufficiently pure for further transformations. 1H-NMR (250 MHz, DMSO) □1.75 (1H, t, J=3.5 Hz), 1.84 (1H, m), 1.92-2.07 (2H, m), 2.15 (1H, dd, J=12.5, 7 Hz), 3.87 (1H, btJ=7 Hz); MS[ISN] 226 [(M-H)-]; mp 124-128° C.; □D20 -61.48° (c=0.90, H2O).

Provenance & Evidence