1,1'-Carbonyldiimidazole → HCID 86604344, compound

HRID 1282514Notes

Reaction equation

HRID 1282514 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1/[CH:5]=[CH:6]/[C:7]([OH:9])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([N:30]([S:40]([C:43]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=1)(=[O:42])=[O:41])[C@H:31]([C:37]([OH:39])=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])[CH:27]([CH3:29])[CH3:28]>C1COCC1.C([O-])([O-])=O.[K+].[K+].Cl>[CH2:26]([N:30]([S:40]([C:43]1[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=1)(=[O:42])=[O:41])[C@H:31]([C:37]([OH:39])=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:7](=[O:9])/[CH:6]=[CH:5]/[C:4]1[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=1[O:2][CH3:1])[CH:27]([CH3:29])[CH3:28]

Participants

7

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 734154(2E)-3-(2-Methoxyphenyl)-2-propenoic acidHCID 69107391HCID 69107391, compound

Product 1

HCID 86604344HCID 86604344, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of trans-2-methoxycinnamic acid (106 mg, 0.55 mmol) and carbonyldiimidazole (89 mg, 0.55 mmol) in THF (3 mL) was stirred at room temperature for 1 h, and then at 40° C. until gas evolution ceased. The mixture was cooled to room temperature and Nα-isobutyl-Nα-(4-nitrobenzenesulfonyl)-L-lysine (212 mg, 0.50 mmol) in solution in 1M K2CO3 was added. The reaction mixture was stirred at room temperature for 3 h, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo and purified by flash chromatography eluting with 70% EtOAc in hexane containing 0.4% AcOH to give the title compound (71% yield).

Workup

  1. customat 40° C.
  2. temperatureThe mixture was cooled to room temperature
  3. stirringThe reaction mixture was stirred at room temperature for 3 h
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography
  8. washeluting with 70% EtOAc in hexane containing 0.4% AcOH

Sources & evidence

ORD record
ord-382542e23fc548f7822ab5f013805991
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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