HCID 10900108, compound → HCID 9794150, compound

The azide (16) (0.12 g, 0.63 mmol) was stirred in methanol (5 ml) at room temperature under hydrogen in the presence of 10% palladium on carbon (10 mg). After 24 h, t.l.c. (5% methanol in ethyl acetate) indicated conversion of the starting material (Rf 0.3) to a single product (Rf 0.0). The reaction mixture was filtered through celite, the solvent removed in vacuo, and the resulting solid purified by ion exchange chromatography with Dowex 50W-X8 using 0.5M ammonia as eluant. After freeze drying, 1-amino-2,5-anhydro-1-deoxy-D-glycero-D-talo-heptitol (5) (95 mg, 88%) was obtained as a yellowish solid. The solid was taken up in water, and the solution neutralised with dilute aqueous hydrochloric acid. Freeze drying, followed by recrystallisation from methanol/chloroform, gave 1-amino-2,5-anhydro-1-deoxy-D-glycero-D-talo-heptitol hydrochloride (5) as a colourless crystalline solid, m.p. 189° C. (dec.). (Found: C, 36.61; H, 7.27; N, 5.42. C7H16O5NCl requires C, 36.61; H, 7.02; N, 6.10%); [α]D20 +38.6° (c 1.0 in CHCl3); δH (D2O) 3.00 (1H, dd, H-1, J1,1' 13.4 Hz, J1,2 8.8 Hz), 3.18 (1H, dd, H-1', J1',2 2.9 Hz), 3.52 (1H, dd, H-7, J6,7 5.0 Hz, J7,7' 12.1 Hz), 3.66 (1H, dd, H-7', J6,7' 2.7 Hz), 3.80 (1H, ddd, H-6, J5,6 9.0 Hz), 3.87 (1H, dd, H-5, J4,5 2.6 Hz), 3.91 (1H, dt, H-2, J2,3 8.4 Hz), 4.05 (1H, dd, H-3, J3,4 4.1 Hz), 4.17 (1H, dd, H-4); δC (D2O) 41.8, 63.1 (2×t, C-1, C-7), 69.0, 71.6, 74.3, 77.2, 79.6 (5×d, C-2, C-3, C-4, C-5, C-6); m/z (NH3, DCI) 194 (M+H+, 100%).

1. filtrationThe reaction mixture was filtered through celite
2. customthe solvent removed in vacuo
3. customthe resulting solid purified by ion exchange chromatography with Dowex 50W-X8 using 0.5M ammonia as eluant
4. customAfter freeze drying

ORD record

ord-045c449f24d54160bb88bfadce2bfd01

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05384417