HCID 54049623, compound → Oxanosine

HRID 5144Notes

Reaction equation

HRID 5144 reaction equation
C1(COC([NH:11][C:12]2[O:13][C:14](=[O:30])[C:15]3[NH:20][CH2:19][N:18]([C@@H:21]4[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]4[OH:23])[C:16]=3[N:17]=2)=O)C=CC=CC=1>[Pd].CN(C=O)C>[CH:19]1[N:18]([C@@H:21]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]2[OH:23])[C:16]2[N:17]=[C:12]([NH2:11])[O:13][C:14](=[O:30])[C:15]=2[N:20]=1

Participants

4

Reactant 1

HCID 54049623HCID 54049623, compound

Product 1

HCID 477547Oxanosine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

10% Palladium on charcoal (172 mg) was added to a solution of 5-[[(phenylmethoxy)carbonyl]amino]-3-(β-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(1H)-one (172 mg, 0.41 mmol) in DMF (7 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 4 h. The mixture was filtered through prewashed Celite and was concentrated under high vacuum. The residue was dissolved in water and filtered through a Millipore Millex-HV filter (0.45 μm). The filtrate was lyophilized to give oxanosine as a white powder: 115 mg, (100%). Crystallization from warm water gave oxanosine (75%) as colorless needles: mp 191°-192° C.; [α]25D -38.7° (c 1, H2O); IR (KBr) 3440-3200, 1802, 1772, and 1550 cm-1 ; MS [(+) FAB]m/z 285 (M+H+); NMR (D2O) δ3.80-3.91 (m, 2), 4.21-4.23 (m, 1), 4.40 (t, 1, J=4.6 Hz), 4.69 (t, 1, J=5.5 Hz), 5.80-5.85 (d, 1, J=5.5 Hz), 7.98 (s, 1); UV max (H2O) 245 nm (ε11760), 287 (8450).

Workup

  1. filtrationThe mixture was filtered through prewashed Celite
  2. concentrationwas concentrated under high vacuum
  3. dissolutionThe residue was dissolved in water
  4. filtrationfiltered through a Millipore Millex-HV
  5. filtrationfilter (0.45 μm)

Sources & evidence

ORD record
ord-36b73a24973348ec866f55e0fe8d820d
Source dataset
uspto-grants-1993_09
Patent number
US05243042

Reaction notes

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