tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate → tert-Butyl (6-cyano-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetate

HRID 1643941Notes

Reaction equation

HRID 1643941 reaction equation
[C:1]([O:5][C:6]([CH:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:9]1[C:13]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=2[N:11](C(OC(C)(C)C)=O)[C:10]1=[O:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O.ClCCl>[C:18]([C:15]1[CH:16]=[CH:17][C:12]2[NH:11][C:10](=[O:27])[N:9]([CH:8]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:13]=2[CH:14]=1)#[N:19]

Participants

4

Reactant 1

HCID 66755109tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate

Product 1

HCID 86642497tert-Butyl (6-cyano-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

2.40 (5.34 mmol) of tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIIc) were dissolved in 200 ml of a 2-percent strength trifluoroacetic acid solution in dichloromethane and stirred at room temperature overnight. The solvent and excess trifluoroacetic acid were removed in vacuo, and the residue was taken up in toluene, concentrated in vacuo and dried.

Workup

  1. customThe solvent and excess trifluoroacetic acid were removed in vacuo
  2. concentrationconcentrated in vacuo
  3. customdried

Sources & evidence

ORD record
ord-c89ddb656e274a59b920ccbc488457cd
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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