1,1'-Carbonyldiimidazole → HCID 118308695, compound

HRID 923492Notes

Reaction equation

HRID 923492 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]([CH3:16])([C:13]([OH:15])=O)[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[NH:32][C:33](=[NH:35])[CH3:34]>CN(C=O)C>[CH3:17][C:9]1([CH3:18])[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:12]([CH3:16])([C:13]2[O:15][N:35]=[C:33]([CH3:34])[N:32]=2)[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 230022953-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acidHCID 178465666HCID 178465666, compound

Product 1

HCID 118308695HCID 118308695, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 430 mg of 3-(tert-butoxycarbonyl)-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid in 4 ml of DMF was added 296 mg of 1,1′-carbonyldiimidazole, followed by stirring at room temperature for 2 hours. To the reaction mixture was added 146 mg of N-hydroxyacetamidine, followed by stirring at room temperature for 1 hour, at 110° C. for 2 hours, and then at 130° C. overnight. The reaction mixture was left to be cooled to room temperature and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 390 mg of tert-butyl 2,2,4-trimethyl-4-(3-methyl-1,2,4-oxadiazol-5-yl)-1,3-oxazolidine-3-carboxylate.

Workup

  1. stirringby stirring at room temperature for 1 hour, at 110° C. for 2 hours
  2. customat 130° C.
  3. customovernight
  4. waitThe reaction mixture was left
  5. temperatureto be cooled to room temperature
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4203084bff3e43d0a95a245939dd47d5
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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