Ethyl Acetate → HCID 57423913, compound

HRID 2064069Notes

Reaction equation

HRID 2064069 reaction equation
CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[NH:17][C:18]([NH:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)=[O:19].C(OCC)(=O)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:15][CH:14]([C:12]1[CH:13]=[CH:8][C:9]2[NH:17][C:18](=[O:19])[N:20]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)[C:10]=2[CH:11]=1)[CH3:16]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 23676156Sodium t-butoxideHCID 57423912HCID 57423912, compound

Product 1

HCID 57423913HCID 57423913, compound

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of tris(dibenzylideneacetone)dipalladium (0) (0.14 g), 1,1′-bis(diphenylphosphino)ferrocene (0.07 g), sodium tert-butoxide (0.4 g) in 1,4-dioxane (10 mL) was stirred under an atmosphere of argon for 10 minutes. 1,1-dimethylethyl 4-[({[2-bromo-4-(1-methylethyl)phenyl]amino}carbonyl)amino]-1-piperidinecarboxylate D33 (2.7 g) was added and the mixture was heated to 90° C. The mixture was stirred at this temperature overnight. The mixture was poured into ethyl acetate which was washed with dilute sodium bicarbonate, brine and dried over sodium sulphate. The solvent was removed and the residue was chromatographed on silica gel eluted with ethyl acetate/hexane 0-50% to give the title compound as a solid. (0.723 g)

Workup

  1. addition(2.7 g) was added
  2. washwas washed with dilute sodium bicarbonate, brine
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed
  5. customthe residue was chromatographed on silica gel
  6. washeluted with ethyl acetate/hexane 0-50%

Sources & evidence

ORD record
ord-3e19aa4c88d84d2cbb3c8a492a3ba132
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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