beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate → 1-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester

HRID 1703726Notes

Reaction equation

HRID 1703726 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:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@@H:25]([O:26][C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:15]1[O:16][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=O)C.P([O-])(OC1C=CC([N+]([O-])=O)=CC=1)(OC1C=CC([N+]([O-])=O)=CC=1)=O>>[CH3:9][O:8][C:6]([C:3]1[N:4]=[CH:5][N:1]([C@@H:14]2[O:36][C@H:35]([CH2:37][O:38][C:39](=[O:46])[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C@@H:25]([O:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:15]2[O:16][C:17](=[O:24])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:2]=1)=[O:7]

Participants

4

Reactant 3

HCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateHCID 5255575Bis(p-nitrophenyl)-phosphateHCID 178499122HCID 178499122, compound

Product 1

HCID 134568041-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-1,2,4-triazole-3-carboxylic acid methyl ester

Procedure

A mixture of methyl 1,2,4-triazole-3-carboxylate (12.7 g., 100 mmole) and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (55.4 g., 110 mmole) was heated in an oil bath maintained at 160-165°. After the sugar had melted, bis(p-nitrophenyl) phosphate (400 mg.) was added with stirring and the mixture was heated under diminished pressure at 160-165° for 15-20 min. Crystallization of the residue from ethyl acetate-ethanol provided 42.5 g. (74.5%) of product with M.P. 137-139°.

Workup

  1. temperaturewas heated in an oil bath
  2. temperaturemaintained at 160-165°
  3. temperaturethe mixture was heated under diminished pressure at 160-165° for 15-20 min
  4. customCrystallization of the residue from ethyl acetate-ethanol
  5. customprovided 42.5 g

Sources & evidence

ORD record
ord-033673a7a2f44b4a9ab789d9c8234e62
Source dataset
uspto-grants-1978_11
Patent number
USRE029835

Reaction notes

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