Hydrogen Sulfide → HCID 178465667, compound

The ethylene analog of canavanine 8, was obtained by treatment of the copper salt of L-canaline (1 mmol, 7), prepared as described for 4, with 2-ethoxyimidazoline (240 mg, 1.8 mmol) in water (5 mL) at 45° C. for 4 days. After adjusting the solution to pH 5.0 with 1N NaOH, hydrogen sulfide was bubbled through for 5 min. The acidic reaction mixture was filtered and the filtrate adjusted to pH 3.4 with 1N NaOH. This solution was applied to a 25 cm3 column of Dowex 50×8 (NH4+) and the resin was washed with distilled water (500 mL) followed by 0.2N NH4OH (400 mL). The ammonia wash was evaporated to dryness by rotary evaporation in vacuo, and the resulting residue was purified by cellulose column chromatography (25×1 cm) by elution with n-BuOH:AcOH:H2O (4:1:1). Fractions containing 8 were combined and the solvent was removed by rotary evaporation in vacuo to give pure 8 (29 mg, 16%) as a glassy solid; [α]D23 =+9.6° (c=2.4, H2O); 1H-NMR (D2O): δ4.08-4.17 (m, 2H, 4-CH2), 3.90 (t, J=6.0 Hz, 1H, 2-CH), 3.80 (s, 4H, NCH2CH2N), 2.27 (dt, J=6.0 Hz, 2H, 3-CH2) ppm; 13C-NMR (CDCl3): δ176.66 (C-1), 164.09 (C=N), 75.72 (C-4), 54.99 (C-2), 45.75 (2×NCH2), 31.51 (C-3) ppm; HRFABMS calcd. for C7H14N4O3 203.1144 (MH+), found 203.1128.

1. customprepared
2. customwas bubbled through for 5 min
3. filtrationThe acidic reaction mixture was filtered
4. washthe resin was washed with distilled water (500 mL)
5. washThe ammonia wash
6. customwas evaporated to dryness by rotary evaporation in vacuo
7. customthe resulting residue was purified by cellulose column chromatography (25×1 cm) by elution with n-BuOH:AcOH:H2O (4:1:1)
8. additionFractions containing 8
9. customthe solvent was removed by rotary evaporation in vacuo

ORD record

ord-43284ef5af464f77a0bac5b7b7f24bed

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859295