1,1'-Carbonyldiimidazole → HCID 58224186, compound

HRID 1241926Notes

Reaction equation

HRID 1241926 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10]([CH3:14])[C:11]([OH:13])=O.C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@:9]1([CH2:15][N:16]2[CH:20]=[N:19][CH:18]=[N:17]2)[O:21][C:11](=[O:13])[C@@H:10]1[CH3:14]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21061645HCID 21061645, compound

Product 1

HCID 58224186HCID 58224186, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

10 g (27 mmol) of (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-[1,2,4]-triazol-1-yl-butyric acid (oxalate salt) were dissolved in 200 ml of tetrahydrofuran and after addition of 5.8 g (35 mmol) 1,1′-carbonyldiimidazole stirred at 60° C. for 3 hours. After evaporation of the solvent the reaction mixture was poured onto 300 ml of aqueous 0.5N-HCl and extracted 3 times with each 300 ml of ethyl acetate. The extract was dried over Na2SO4 and evaporated. 7.1 g (94% yield) of (3R,4R)-4-(2,5-difluoro-phenyl)-3-methyl-4-[1,2,4]triazol-1-ylmethyl-oxetan-2-one resulted.

Workup

  1. customAfter evaporation of the solvent the reaction mixture
  2. additionwas poured onto 300 ml of aqueous 0.5N-HCl
  3. extractionextracted 3 times with each 300 ml of ethyl acetate
  4. dry with materialThe extract was dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b45a4297882540ae887497a1a0d66cbe
Source dataset
uspto-grants-2006_10
Patent number
US07115643B2

Reaction notes

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