Hydrochloric Acid → HCID 15280418, compound

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).

1. concentrationwas concentrated
2. customto afford a viscous syrup
3. temperaturecooled in an ice bath
4. concentrationconcentrated
5. additionThe residue was diluted with 200 mL of ethyl acetate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated
8. customthe residue was chromatographed on a 5×27 cm silica gel column
9. washeluting first with 85:14:1 CHCl3EtOH

ORD record

ord-0cab0c8499c2427da0e12dd9ec3c2a26

Source dataset

uspto-grants-1995_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05401880