(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate → Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate

HRID 478764

Reaction equation

HRID 478764 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.C(O[C@H:14]1[O:26][C@@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:15]1[O:16][C:17](=[O:19])[CH3:18])(=O)C>[N+](C1C=CC(OP([O-])(OC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1)([O-])=O.O>[C:17]([O:16][C@H:15]1[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:26][C@@H:14]1[N:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1)(=[O:19])[CH3:18]

Participants

5

Reactant 2

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateHCID 178499122HCID 178499122, compound

Product 1

HCID 10691464Methyl 1-(2,3,5-Tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylateYield 66%

Reagents, catalysts & solvents 2

HCID 5255575Bis(p-nitrophenyl)-phosphateCatalystHCID 962WaterSolvent

Procedure

A mixture of methyl 1,2,4-triazole-3-carboxylate (0.64 g, 5 mmol), 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose (2) (1.5 g, 4.72 mmol) and bis(p-nitrophenyl)-phosphate (20 mg) were placed in a pear shaped flask and placed in a preheated oil bath at (160-165° C.). The flask was connected to a water aspirator and kept at 160-165° C. (oil bath temperature) under reduced pressure with stirring for 25 min. The reaction mixture was removed, cooled and diluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL). The product was extracted in EtOAc. The organic extract was washed with water (100 mL) and brine (50 mL), dried and evaporated to dryness. The residue that obtained was purified by flash column of silica gel using CHCl3→EtOAc as the eluent. The pure fractions were collected and evaporated to dryness to give 1.2 g (66%) of pure product: 1H NMR (CDCl3) δ2.10 (3s, 9H, 3 COCH3), 3.98 (s, 3H, OCH3), 422 (m, 1H), 4.46 (m, 2H), 5.54 (t, 1H), 5.76 (m, 1H), 6.04 (d, 1H, C1′H), and 8.38 (s, 1H, C3H). Anal Calc. for C15H19N3O9 (385.22): C, 46.75; H, 4.97; N,10.91. Found: C, 46.82; H, 4.57; N=10.71.

Workup

  1. customwere placed in a pear shaped flask
  2. customplaced in a preheated oil bath at (160-165° C.)
  3. customkept at 160-165° C.
  4. customThe reaction mixture was removed
  5. temperaturecooled
  6. additiondiluted with EtOAc (150 mL) and sat. NaHCO3 (100 mL)
  7. extractionThe product was extracted in EtOAc
  8. extractionThe organic extract
  9. washwas washed with water (100 mL) and brine (50 mL)
  10. customdried
  11. customevaporated to dryness
  12. customThe residue that obtained
  13. customwas purified by flash column of silica gel
  14. customThe pure fractions were collected
  15. customevaporated to dryness

Sources & evidence

ORD record
ord-eb1cae2f0a5e4ea2bd585e757c6ffbc9
Source dataset
uspto-grants-2003_11
Patent number
US06642206B2

Linked notes

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