HCID 68157210, compound → HCID 58459222, compound

HRID 242902Notes

Reaction equation

HRID 242902 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=1[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[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:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:13]2[CH:14]=[CH:15][C:16]([F:18])=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157210HCID 68157210, compound

Product 1

HCID 58459222HCID 58459222, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(5-fluoro-2-phenylaminophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester (2.15 mmol) in AcOH (10 mL) was stirred for 18 h at 70° C. After cooling to RT, the volatiles were evaporated in vacuo and the residue partitioned between EtOAc and a saturated aqueous solution of NaHCO3. The organic fraction was washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) to afford the title compound as an orange oil (661 mg, 86% over two steps). LCMS (Method J): RT 3.52 min [M+H]+ 356.1.

Workup

  1. customthe volatiles were evaporated in vacuo
  2. customthe residue partitioned between EtOAc
  3. washThe organic fraction 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-fbf7809cc1354e39b4144b5fc483c8db
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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