반응 #969841

반응 방정식

acetonitrile

water

11-azido-3,6,9-trioxaundecanamine

diglycolic anhydride

→

yellow syrup

17-Azido-5-oxo-6-aza-3,9,12,15-tetraoxaheptadecanoic acid

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.WAITgradient 4-16% B over 20 min
2. 2
   농축The solution was concentrated

실험 절차

To a solution of 11-azido-3,6,9-trioxaundecanamine (10.9 g, 50.0 mmol) in dichloromethane (100 ml) was added diglycolic anhydride (6.38 g, 55.0 mmol). The reaction mixture was stirred overnight. HPLC analysis (column Vydac 218TP54; solvents: A=water/0.1% TFA and B=acetonitrile/0.1% TFA; gradient 4-16% B over 20 min; flow 1.0 ml/min; UV detection at 214 and 284 nm), showed complete conversion of starting material to a product with retention time 18.3 min. The solution was concentrated to give quantitative yield of a yellow syrup. The product was analysed by LC-MS (ES ionisation) giving [MH]+ at 335 as expected. 1H (500 MHz) and 13C (125 MHz) NMR spectroscopy was in agreement with structure The product was used in the next step without further purification.

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