Hydrochloric Acid → HCID 15280418, compound

Participants

Reaction Steps

To a solution of sodium pantothenate (10.0 g, 41.5 mmol) and allylamine (3.20 mL, 2.44 g, 42.6 mmol) in 50 mL of water was added 7.1 mL of concentrated aqueous HCl The resulting mixture (pH 2.0-2.5) was concentrated to afford a viscous syrup. The syrup was diluted with 50 mL of DMF, cooled in an ice bath, and treated with diethylcyanophosphonate (6.40 mL, 6.88 g, 42.2 mmol, 1.02 eq.) followed by triethylamine (13.0 mL, 9.44 g, 93.3 mmol, 2.25 equiv). The mixture was stirred at 0°-10° C. for 1 h and then concentrated. The residue was diluted with 200 mL of ethyl acetate and filtered. The filtrate was concentrated and the residue was chromatographed on a 5×27 cm silica gel column, eluting first with 85:14:1 CHCl3EtOH:aq NH4OH and then with 77.5:21:1.5 CHCl3 :EtOH:aq NH4OH to afford 8.03 g (75%) of pantothenic acid allyl amide as a pale yellow oil: TLC (85:14:1 CHCl3 :EtOH:aq NH4OH) Rf 0.40; 1H NMR (D2O) ∂5.83 (1, m), 5.17 (1H, m) 5.13 (1H, m), 3.96 (1H, s), 3.77 (2H, m), 3.51 (2H, m), 3,49 (1H, d, J=11.4 Hz), 3.37 (1H, d, J=11.4 Hz), 2.51 (2H, t, J=6.4 Hz), 0.90 (3H, s), 0.86 (3H, s).

Provenance & Evidence