Ethanol → HCID 54402306, compound

Participants

Reaction Conditions

Reaction Steps

L-Asparagine monohydrate 1* (37.5 g, 0.25 mol) was dissolved in 3M H2SO4 (330 ml) and treated with KBr (39.3 g, 0.75 mol). The solution was stirred and cooled in an ice-MeOH bath to ca. -10° C. Some precipitation occurred. A solution of NaNO2 (21.6 g, 0.31 mol) in H2O (38 ml) was added dropwise over 80 minutes. The internal temperature was kept at -10° to -5° during the addition and for 90 minutes afterward. The mixture was filtered and the solid portion washed with ice cold H2O (3x) and dried overnight to give the product 2* (31.64 g, 65%) as an off-white solid: [α]D =-67.8° (C 4.51, EtOH). ##STR93##

Provenance & Evidence