p-Toluenesulfonic acid monohydrate → HCID 23257307, compound

Participants

Reaction Steps

Compound 8 (330 mg, 0.317 mmol) was stirred at r.t. in CH2Cl2/MeOH 4:1 (6 ml) containing 2% of TsOH.H2O for 15 min. Then the mixture was diluted with CH2Cl2 (70 ml) and washed with sat. NaHCO3 soln. (2×40 ml), the aq. phase reextracted with CH2Cl2, the combined org. layer dried (MgSO4) and evaporated, and the residue purified by FC (silica gel, 12×2 cm, CHCl3, CHCl3+5% MeOH). The obtained oily substance was treated with small amounts of Et2O/MeCN 2:1 to give 215 mg (88%) of 10. Amorphous solid. UV (CH2Cl2); 272 (sh, 4.36), 267 (4.41). 1H-NMR (CDCl3):8.71, 8.21-8.15 (2m, H—C(8), H—C(2), 2 H o to NO2,NH(ade)); 7.45 (d, 2 H m to NO2); 6.03 (d, H—C(1′)); 5.58 (m, H—C(2′)); 5.55 (br., NH(CH2)5CO); 5.0 (br., OH—C(5′)); 4.65-4.50 (m, t, H—C(4′), OCH2CH2); 4.12, 3,75 (2m, 2 H—C(5′)); 3.25(q, 1 CH2 of NH(CH2)5CO); 3.15 (t, OCH2CH2);2.9, 2.25 (2m, 2 H—C(3′)); 2.35, 2.15 (2t, 2 CH2 of NH(CH2)5CO), 2 H of Me(CH2)12CO); 1.7-1.15 (m, 28 H, 2 CH2 of NH(CH2)5CO, Me(CH2)12CO); 0.87 (t, Me(CH2)12CO)12 Anal. calc. for C39H57N7O9 ½ H2O (782.02): C 59.90, H 7.41, N 12.54; found: C 60.27, H 7.66, N 12.06.

Provenance & Evidence