N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 178453838, compound

Participants

Reaction Steps

109.2 Grams (0.27 mol) of H-Arg-CHA.2HCl was dissolved in 290 ml of DMF and then 70.2 ml (0.54 mol) of NEM was added thereto, followed by further addition of 81.7 g (0.3 mol) of BOC-Gly-OSu at 0° to 5° C. and the reaction was carried out at room temperature for 18 hours. After the reaction was completed, the DMF was removed by evaporation under a reduced pressure and the residue was dissolved in 500 ml of MeOH and reprecipitated in 8 liters of AcOEt. The crystals precipitated were collected by filtration and dried to obtain 135.8 g (100%) of BOC-Gly-Arg-CHA.HCl. Rf1 =0.46. Melting point: 214.5° C. (decomposed). [α]D20 -22 (C=1, MeOH)

Provenance & Evidence