Tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate → tert-Butyl (6-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)acetate

HRID 1631949Notes

Reaction equation

HRID 1631949 reaction equation
[C:1]([O:5][C:6]([CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[N:11](C(OC(C)(C)C)=O)[C:10]1=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]>FC(F)(F)C(O)=O.ClCCl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]2[NH:11][C:10](=[O:26])[N:9]([CH2:8][C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[C:13]=2[CH:14]=1

Participants

4

Reactant 1

HCID 66754580Tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Product 1

HCID 86642492tert-Butyl (6-chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)acetate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.8 g (4.70 mmol) of tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIIg) in 100 ml of 2% trifluoroacetic acid in dichloromethane was stirred at room temperature for 16 h. The solvent was removed in vacuo and the residue was dried in vacuo. Yield: 1.32 g (100%) of colorless solid

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-ae7d5fb9daf04e8fbedcbe62608cad8c
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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