Dimethylformamide → 2-[(tert-Butoxy)carbonylamino]-N-(phenylmethoxy)acetamide

Participants

Reaction Conditions

Reaction Steps

HCl·NH2OBzl (11.2 g; 70.2 mmol) was suspended in DMF (100 ml) and TEA (11.2 ml; 80.0 mmol) was added dropwise under ice-cooling. HOBt (7.43 g; 55.0 mmol) and Boc-Gly-OH (8.76 g; 50.0 mmol) were then added and the mixture was cooled with a coolant at -20° C. DCC (14.5 g; 70.2 mmol) dissolved in CH2Cl2 (70 ml) was added dropwise. After the dropwise addition, the reaction was allowed to proceed for 1 hour at -10° C. and overnight in a refrigerator. Insolubles were filtered off and the solvent was distilled off under reduced pressure. The residue was dissolved in AcOEt and then washed successively with water, 1N-HCl, water, 10% Na2CO3 and water. The solution was dried over anhydrous MgSO4 and the solvent was distilled off under reduced pressure. The residue was purified by chromatography on silica gel (Fuji Davison BW 200, 300 g; eluted with AcOEt: n-Hexane (=1:1) mixed solvent) to give Boc-Gly-NHOBzl (13 g; 93%) as a pale yellow oil.

Provenance & Evidence