Hydrochloric Acid → HCID 86762374, compound

Participants

Reaction Steps

To a reddish solution of the above dicetonide 14 (1.00 mmol) in THF (25 mL), was added 1.0 N HCl (5 mL) and stirred for 5 h in an atmosphere of argon. Most of the THF was removed from the reaction mixture, neutralized by 1.0 N NaOH, and concentrated in vacuo. The crude product (2.40 g) was subjected to preparative RP-HPLC (XBridge, 10-50% B/12 min) to afford diastereomeric 13 (0.554 g, 74%) as red gum: UV (λmax) 499 nm; 1H NMR (CDCl3) 8.66, 8.56 (2 t, 2), 6.24 (broad s, 6), 4.40 (t, 1.5, J=4.2, 5.2), 4.23-4.15 (m, 1.5), 3.97-3.90 (m, 3), 3.70-3.50 (m, 36), 3.37, 3.36 (2 s, 6), 1.98-1.90 (quintet, 4); RP-HPLC (254 nm) 98% (tR=17.43 min, 5-50% B); RP-LC/MS (ESI) m/z 754.5 (M+H)+ (tR=3.58 min). HRMS (ESI) m/z calculated for C32H61N6O14 (M+H)+ 753.4240. found 753.4252.

Provenance & Evidence