Sodium Carbonate → HCID 18672407, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 649 mg (2.27 mmol) 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl alcohol from the previous step in 5.0 mL THF at 0° C. was added 0.674 mL (3.13 mmol) of DPPA and 0.468 mL (3.13 mmol) of DBU and the reaction was stirred at 0° C. for 10 min, then at room temperature. After 3 h the reaction was treated with saturated aqueous sodium carbonate and extracted with ethyl acetate (3×). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness in vacuo to give 963 mg of a crude oil. Flash chromatography on silica gel (15% ethyl acetate in hexane) gave tert-butyl 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl azide as a colorless oil: 1H NMR (DMSO-d6, 400 MHz): δ 7.44 (d, 1H, J=1.8 Hz), 7.36 (dd, 1H, J=2.0 and 8.2 Hz), 7.26 (d, 1H, J=8.1 Hz), 6.92 (br t, 1H, J=5.5 Hz), 4.53 (s, 2H), 3.10 (dt, 2H, J=6.3 and 7.6 Hz), 2.73 (t, 2H, J=7.3 Hz), 1.36 (s, 9H); MS (Electrospray): M+Na=333.0; TLC Rf=0.32 (15% ethyl acetate in hexane).

Provenance & Evidence