Sodium Hydroxide → HCID 66818226, compound

HRID 1755027Notes

Reaction equation

HRID 1755027 reaction equation
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]([C:31](=[O:33])[NH2:32])([NH:16][C:17](=O)/[CH:18]=[CH:19]/[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2([N:16]=[C:17](/[CH:18]=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[NH:32][C:31]2=[O:33])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66817673HCID 66817673, compound

Product 1

HCID 66818226HCID 66818226, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 6 N aqueous sodium hydroxide solution was added to a solution of 4-carbamoyl-4-[(E)-3-(3-trifluoromethyl-phenyl)-acryloylamino]-piperidine-1-carboxylic acid tert-butyl ester (961 mg, 2.27 mmol) in ethanol (20 ml), and the mixture was stirred at room temperature for 22 hours. The reaction solution was quenched with saturated ammonium chloride and then extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 4-oxo-2-[(E)-2-(3-trifluoromethyl-phenyl)-vinyl]-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (706 mg, 73%).

Workup

  1. customThe reaction solution was quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was sequentially washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af820e150f8e4d968c6730fee577951c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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