Triethylamine → HCID 135678277, compound

Participants

Reaction Steps

Copper iodide (38.1 mg, 0.2 mmol), triethylamine (2.8 ml, 2 mmol), tetrakis(triphenylphsophine)palladium(0) (40.5 mg, 0.1 mmol) and 1-hexyne (492 mg, 6 mmol) are added to an argon-flushed solution of compound (58) (390 mg, 1 mmol in 5 ml of dried DMF), and the solution is stirred at room temperature for 24 h. It is then evaporated and the residue is loaded onto a silica gel column (5×25 cm). Title compound (65) is obtained following stepwise elution with 5%, 10% and 20% MeOH in CH2Cl2. Recrystallization from MeCN affords a colorless solid (120 mg, 35%). 1H-NMR ([D6 ] DMSO): δ=0.94 (m, CH3), 1.49, 2.38 (m, CH2), 2.0 (M, Hα --C(2')), 2.35 (m, Hβ --C(2')), 3.50 (m, H2 --C(5')), 3.76 (m, H--C(4')), 4. (m, H--C(3')), 4.88 (t, 5'-OH), 5.18 (d, J=3.5, 3'-OH), 6.27 (m, H--C(1')+NH2), 7.13 (s, H--C(6)), 10.34 (br., NH). MS: m/e 346 (M+).

Provenance & Evidence