Lithium Hydroxide → HCID 71288128, compound

Participants

Reaction Steps

CDI (1.76 g, 10.78 mmol) was added portion-wise to a stirred solution of 2-acetoxyacetic acid (1.27 g, 10.78 mmol) in NMP (5 mL). After 10 minutes, (Z)-tert-butyl 5-(N′-hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) (1.43 g, 5.39 mmol) was added in one portion and stirred for another hour at room temperature. The solution was then heated via microwave at 125° C. for 15 minutes. The solution was partitioned with EtOAc and water. The organic phase was separated, dried over Na2SO4 and concentrated to give a residue which was dissolved in THF/MeOH/H2O (3:2:1, 5 mL) and followed by addition of 6N LiOH (5.4 mL). The resulting mixture was stirred for 10 minutes. Then aqueous 2M NaHCO3 (30 mL) was added and the solution was extracted with EtOAc. The organic layers were dried over Na2SO4 and concentrated to give a residue which was purified over silica gel to afford tert-butyl (5-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamate (137). MS m/z 306.0 (M+1)+.

Provenance & Evidence