HCID 68157151, compound → HCID 68158133, compound

HRID 243267Notes

Reaction equation

HRID 243267 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]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[NH:19][CH:20]1[CH2:23][CH:22]([C:24]#[N:25])[CH2:21]1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10]1[N:19]([CH:20]2[CH2:23][CH:22]([C:24]#[N:25])[CH2:21]2)[C:13]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:12]=2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157151HCID 68157151, compound

Product 1

HCID 68158133HCID 68158133, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of {(S)-1-[2-(3-cyanocyclobutylamino)-4-fluorophenylcarbamoyl]-ethyl}carbamic acid tert-butyl ester (0.31 g, 0.83 mmol) in acetic acid (5 mL) was stirred at 70° C. for 16 hours and then at 80° C. for 8 hours. The mixture was concentrated in vacuo and the residue dissolved in DCM then washed with saturated aqueous NaHCO3 and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (Si—PPC; eluting with ethyl acetate in cyclohexane 0-100%) to give the title compound as colourless gum (0.21 g, 73%). LCMS (Method J): RT 2.87 min [M+H]+ 358.0

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DCM
  3. washthen washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (Si—PPC; eluting with ethyl acetate in cyclohexane 0-100%)

Sources & evidence

ORD record
ord-6ddbb8d4335d47559cb13570db07ea07
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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