tert-butyl N-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propyl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: preparation from 1-(tert-butoxycarbonylamino)-4,7,10-trioxa-13-tridecanamine (5 g) and succinic anhydride (1.98) gave 7 g crude product. LCMS (Method 6): Rt 3.34 min; m/z (M+1) 421 Calcd: 421

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 25 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing tert-butyl 3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propylcarbamate (amine, 160 mg, 0.5 mmol), 2-azidoacetic acid (56 mg, 0.55 mmol, in 50% DCM solution), NaHCO3 (168 mg, 2 mmol), and 1 mL DMF was added EDC (115 mg, 0.6 mmol). The mixture was stirred at rt for 3 h and concentrated in vacuo. The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane) to afford compound 141 as a clear oil (130 mg, 65%). MS (ESI) m/z 426 (M+Na+). To a 25 mL round bottomed flask equipped with a magnetic stir bar concentrated in vacuo The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 25 mL round bottomed flask equipped with a magnetic stir bar, rubber septum, and argon inlet containing tert-butyl 3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propylcarbamate (amine, 160 mg, 0.5 mmol), 2-azidoacetic acid (56 mg, 0.55 mmol, in 50% DCM solution), NaHCO3 (168 mg, 2 mmol), and 1 mL DMF was added EDC (115 mg, 0.6 mmol). The mixture was stirred at rt for 3 h and concentrated in vacuo. The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane) to afford compound 141 as a clear oil (130 mg, 65%). MS (ESI) m/z 426 (M+Na+). To a 25 mL round bottomed flask equipped with a magnetic stir bar concentrated in vacuo The crude product was purified by silica chromatography (gradient 5% to 90% EtOAc in hexane)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: preparation from 1-(tert-butoxycarbonylamino)-4,7,10-trioxa-13-tridecanamine (5 g) and succinic anhydride (1.98) gave 7 g crude product. LCMS (Method 6): Rt 3.34 min; m/z (M+1) 421 Calcd: 421