HCID 68157210, compound → HCID 58459222, compound

HRID 242867Notes

Reaction equation

HRID 242867 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:6]([NH:8][C:9](=O)[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH:7]=1>CC(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]([C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])=[N:8][C:6]=2[CH:7]=1

Participants

3

Reactant 1

HCID 68157210HCID 68157210, compound

Product 1

HCID 58459222HCID 58459222, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of (S)-tert-butyl 1-(5-fluoro-2-(phenylamino)phenylamino)-1-oxopropan-2-ylcarbamate (2.15 mmol) in AcOH (10 mL) was stirred for 18 h at 70° 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 organic layer was washed with brine, dried (MgSO4) and then concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) affording (S)-tert-butyl 1-(5-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)ethylcarbamate as an orange oil (661 mg, 86% over two steps). LCMS: RT 3.52 min [M+H]+ 356.1

Workup

  1. customvolatiles were evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-53265c4394a34be59b17b0e7b29462b2
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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