Methylamine → Methylamino-PEG3-t-butyl ester

Participants

Reaction Conditions

Reaction Steps

Into a 250-mL sealed bottle was placed a solution of tert-butyl 3-(2-(2-(2-(tosyloxy)ethoxy)ethoxy)ethoxy)propanoate (14 g, 32.41 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) followed by CH3NH2 (66.9 g, 712.16 mmol, 21.98 equiv, 33% in ethanol) and the resulting solution was stirred overnight at 50° C. The resulting mixture was concentrated under vacuum, dissolved in 150 mL of dichloromethane and then washed with 2×150 mL of water and 1×150 mL of brine. The organic layer was dried over sodium sulfate and concentrated under vacuum to afford 8.2 g (87%) of tert-butyl 3-(2-(2-(2-(methylamino)ethoxy)ethoxy)ethoxy)propanoate as yellow oil.

Provenance & Evidence