Acetic Acid → HCID 23257309, compound

Participants

Reaction Steps

Compound 10 (160 mg, 0.208 mol) was co-evaporated twice with abs. pyridine and then dissolved in abs. pyridine (2 ml). DBU (158 mg, 1.04 mmol) was added, the mixture kept at r.t. for 18 h, then AcOH (62 mg, 1.04 mmol) added, and the soln. evaporated. The residue was diluted with CHCl3 (80 ml) and washed with a 10% citric acid soln. (2×50 ml), the aq. phase reextracted with CHCl3, the combined org. layer dried (MgSO4), evaporated, and co-evaporated with toluene, and the residue precipitated by MeOH and washed with Et2O: 103 mg (86%) of 12. UV (CH2Cl2: 259 (4.16). 1H-NMR ((D6)DMSO): 8.33, 8.13 (2s, H—C(8), H—C(2)); 7.68 (t, NH(CH2)5CO); 7.25 (s, NH2); 6.05 (d, H—C(1′)); 5.60 (m, H—C(2′)); 5.11 (t, OH—C(5′)); 4.32 (m, H—C(4′)); 3.65, 3.47 (2m, 2 H—C(5′)); 2.95 (q, 1 CH2 of NH(CH2)5CO); 2.6, 2.15 (2m, 2 H—C(3′)); 2.34, 2.00 (2t, 2 CH2 of NH(CH2)5CO, 2 H of Me(CH2)12Co); 1.65-1.15 (m, 28 H, 2 CH2 of NH(CH2)5CO, Me(CH2)12CO); 0.83 (t, Me(CH2)12CO). Anal. calc. for C30H50N6O5 ½ H2O (583.76): C 61.72, H 8.81, N. 14.39; found C 62.04, H 9.07, N 13.85.

Provenance & Evidence