[(S)-1-(2-Chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester → [(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester

HRID 242794Notes

Reaction equation

HRID 242794 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[C:17]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:25])[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:25])[C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157659[(S)-1-(2-Chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester

Product 1

HCID 68157799[(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl esterYield 93.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(2-chloro-6-phenylaminophenylcarbamoyl)ethyl]carbamic acid tertbutyl ester (1.58 g, 4.05 mmol) in AcOH (25 mL) was stirred for 18 h at 65° C. After cooling to RT, volatiles were evaporated under reduced pressure and the residue was partitioned between EtOAc and a saturated solution of NaHCO3. The aqueous phase was further extracted with EtOAc and the combined organic layers were washed with brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM) affording [(S)-1-(4-Chloro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]carbamic acid tertbutyl ester as an off-white solid (1.41 g, 93%). LCMS: RT 3.90 min [M+H]+ 372.2.

Workup

  1. customvolatiles were evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc
  3. extractionThe aqueous phase was further extracted with EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-2% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record
ord-72b877a8e78c4b36944f472673ae8c04
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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