Dicyclohexylcarbodiimide → 3-[(Allyloxycarbonylaminomethyl)carbonylamino]methyl imidazo[5,1-b]thiazole

HRID 1603446Notes

Reaction equation

HRID 1603446 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6])[CH:2]=[CH2:3].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:37][CH2:38][C:39]1[N:40]2[CH:46]=[N:45][CH:44]=[C:41]2[S:42][CH:43]=1>CN(C=O)C.ClCCl>[CH2:1]([O:4][C:5]([NH:7][CH2:8][C:9]([NH:37][CH2:38][C:39]1[N:40]2[CH:46]=[N:45][CH:44]=[C:41]2[S:42][CH:43]=1)=[O:11])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11964402N-[(allyloxy)carbonyl]glycineHCID 196051553-Aminomethylimidazo[5,1-b]thiazole

Product 1

HCID 196051913-[(Allyloxycarbonylaminomethyl)carbonylamino]methyl imidazo[5,1-b]thiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A 5 ml portion of a dichloromethane solution containing 307 mg of N-allyloxycarbonyl glycine was cooled on ice, and 287 mg of 1-hydroxybenzotriazole and 438 mg of 1,3-dicyclohexylcarbodiimide were further added to the cooled mixture, followed by stirring under ice-cooling for 2 hours. Further, 5 ml of dichloromethane containing 3-aminomethylimidazo[5,1-b]thiazole and 10 ml of DMF were added thereto, and dichloromethane was then evaporated under reduced pressure, followed by stirring at room temperature for 1.5 hours. To the reaction solution, a saline solution was added, and extraction was then carried out three times with ethyl acetate. Afterward, the resulting organic layer was dried over anhydrous magnesium sulfate, and after the removal of the drying agent by filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by a silica gel column chromatograph to obtain 387 mg of the title compound.

Workup

  1. additionwere further added to the cooled mixture
  2. temperaturecooling for 2 hours
  3. additionwere added
  4. customdichloromethane was then evaporated under reduced pressure
  5. stirringby stirring at room temperature for 1.5 hours
  6. additionTo the reaction solution, a saline solution was added
  7. extractionextraction
  8. dry with materialAfterward, the resulting organic layer was dried over anhydrous magnesium sulfate
  9. customafter the removal of the drying agent
  10. filtrationby filtration
  11. customthe solvent was evaporated under reduced pressure
  12. customThe resulting residue was purified by a silica gel column chromatograph

Sources & evidence

ORD record
ord-106bb707a71a4f8e89762f4cc5824ba0
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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