Lithium Hydroxide → HCID 15454797, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 118 (12.7 mg, 0.029 mmol) in THF-H2O--CH3OH (3:1:1, 0.45 mL) was treated with LiOH (6.0 mg, 0.14 mmol, 5.0 equiv) and the mixture was stirred at 25° C. for 2 h before the solvent was removed in vacuo. The crude product was dissolved in H2O and was acidified to pH 0.5 with the addition of 10% aqueous HCl. The product was extracted with 30% isopropanol-CHCl3 (7×1.2 mL), and the combined extracts were concentrated to afford 119 (11.9 mg, 11.9 mg theoretical, 100%) as an off white solid which was sufficiently pure to use in the next reaction directly: 1H NMR (CD3OD, 400 MHz) 8.16 (s, 1H), 8.14 (s, 1H), 3.71 (t, J=6.8 Hz, 2H), 3.51 (t, J=7.0 Hz, 2H), 3.30 (t, 2H, overlapped with CH3OH), 2.58 (t, J=7.2 Hz, 2H), 2.10 (s, 3H), 1.92 (tt, J=7.2, 7.0 Hz, 2H); IR (film)max 3346, 3102, 2916, 1656, 1543, 1480, 1436, 1362, 1294, 1240, 1128, 1054 cm-1 ; FABHRMS (NBA) m/z (M++H, C15H18N4O4S3 requires 415.0568).

Provenance & Evidence