N-[tert-butoxycarbonyl]-L-serine → HCID 178454224, compound

Participants

Reaction Steps

(S)-2-((tert-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (226 mg, 1.10 mmol) was dissolved in N,N-dimethylformamide (5 mL) and 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid-hexafluorophosphate (440 mg, 1.10 mmol) was added. The reaction was stirred for 10 minutes then 4-(tert-butyl)benzene-1,2-diamine (164 mg, 1.00 mmol) was added and the reaction mixture stirred for 18 hours. The reaction mixture was diluted with water and extracted twice with ethyl ether. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo. The residue was dissolved in 1,2-dichloroethane and anhydrous magnesium sulfate was added. The reaction was stirred at 65° C. for 18 hours to complete the dehydration. The reaction mixture was filtered and loaded directly onto a 4 g silica gel column for purification. The column was eluted with 0-10% methanol in dichloromethane to afford 73 mg of product as a white solid.

Provenance & Evidence