1,1'-Carbonyldiimidazole → HCID 22663495, compound

HRID 392641Notes

Reaction equation

HRID 392641 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([O:23][CH2:24][C@@H:25]2[O:30][C:29]3[C:31]([OH:40])=[C:32]([NH:35][C:36]([O:38]C)=O)[CH:33]=[CH:34][C:28]=3[O:27][CH2:26]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C(Cl)Cl>[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:20]([O:23][CH2:24][CH:25]2[CH2:26][O:27][C:28]3[CH:34]=[CH:33][C:32]4[NH:35][C:36](=[O:38])[O:40][C:31]=4[C:29]=3[O:30]2)(=[O:22])=[O:21])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 86587694HCID 86587694, compound

Product 1

HCID 22663495HCID 22663495, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1′-Carbonyldiimidazole (6.45 g, 39.6 mmole) was added to a solution of {(2R)-8-hydroxy-7-[(methoxycarbonyl)amino]-2,3-dihydro-1,4-benzodioxin-2-yl}-methyl 4-methylbenzenesulfonate (5.40 g, 13.2 mmole) in methylene chloride (400 mL), the solution was refluxed for 4 hours under nitrogen. The solvent was then removed in vacuum and was replaced with 2N aqueous HCl (150 mL). After the mixture had been stirred for 0.5 hour at room temperature, a white solid precipitate, the (R)-enantiomer of the title compound, was removed by filtration, and was dried under high vacuum (5.0 g, >99%).

Workup

  1. temperaturethe solution was refluxed for 4 hours under nitrogen
  2. customThe solvent was then removed in vacuum
  3. customa white solid precipitate, the (R)-enantiomer of the title compound, was removed by filtration
  4. customwas dried under high vacuum (5.0 g, >99%)

Sources & evidence

ORD record
ord-59665b144af448a68dccc15e7a071863
Source dataset
uspto-grants-2004_10
Patent number
US06800648B2

Reaction notes

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