Water → 5-amino-4-cyano-1-(2,3,5-tri-O-propionyl-beta-D-ribofuranosyl)imidazole

HRID 847763Notes

Reaction equation

HRID 847763 reaction equation
[NH2:1][C:2]1[N:6]([C@@H:7]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:27])[CH2:25][CH3:26])[C@@H:14]([O:15][C:16](=[O:19])[CH2:17][CH3:18])[C@H:8]2[O:9][C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[N:4][C:3]=1[C:28]([NH2:30])=O.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O.O>ClCCl>[NH2:1][C:2]1[N:6]([C@@H:7]2[O:21][C@H:20]([CH2:22][O:23][C:24](=[O:27])[CH2:25][CH3:26])[C@@H:14]([O:15][C:16](=[O:19])[CH2:17][CH3:18])[C@H:8]2[O:9][C:10](=[O:13])[CH2:11][CH3:12])[CH:5]=[N:4][C:3]=1[C:28]#[N:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 128763565-amino-1-(2,3,5,-tri-O-propionyl-beta-D-ribofuranosyl)imidazole-4-carboxamide

Product 1

HCID 129475215-amino-4-cyano-1-(2,3,5-tri-O-propionyl-beta-D-ribofuranosyl)imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 840 g of 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carboxamide, 5.4 l of dichloromethane and 1.38 l of triethylamine was cooled to 0° C. or less, and a solution of 196 ml of phosphorus oxychloride in dichloromethane (1.8 l) was added dropwise thereto while maintaining the temperature below 0° C. After stirring for 1.5 hours, 2 l of water was added to the mixture below 0° C. and the dichloromethane layer was separated. The dichloromethane layer was washed successively with 2 l each of water, twice with 2 l of 1 N hydrochloric acid, and twice with 2 l each of a saturated aqueous sodium chloride solution, and then concentrated to dryness under reduced pressure to obtain 5-amino-1-(2,3,5-tri-O-propionyl-β-D-ribofuranosyl)imidazole-4-carbonitrile as a yellow brown viscous syrup.

Workup

  1. temperaturewhile maintaining the temperature below 0° C
  2. customthe dichloromethane layer was separated
  3. washThe dichloromethane layer was washed successively with 2 l each of water, twice with 2 l of 1 N hydrochloric acid
  4. concentrationtwice with 2 l each of a saturated aqueous sodium chloride solution, and then concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7ce63a3ee25443f986a200fd30fe5f7b
Source dataset
uspto-grants-1981_10
Patent number
US04293690

Reaction notes

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