Hydrochloric Acid → HCID 66818449, compound

HRID 1754908Notes

Reaction equation

HRID 1754908 reaction equation
[OH-:1].[Na+].OO.[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[F:29])([C:18]#[N:19])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].Cl>C1COCC1>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]([C:18](=[O:1])[NH2:19])([NH:20][C:21](=[O:30])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[F:29])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 66816333HCID 66816333, compound

Product 1

HCID 66818449HCID 66818449, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 N NaOH (8.60 ml, 8.60 mmol) and a 30% H2O2 solution (4.30 ml) were added to a solution of 4-(3-chloro-2-fluoro-benzoylamino)-4-cyano-piperidine-1-carboxylic acid tert-butyl ester (1.63 g, 4.28 mmol) in THF (8.60 ml) at room temperature, and the mixture was stirred at room temperature for two hours. The reaction mixture was adjusted to pH 6 by adding 2 N HCl and then extracted with ethyl acetate three times. The organic layers were sequentially washed with H2O (×2) and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was triturated with H2O, and the solid was collected by filtration. The resulting solid was washed with Et2O and then dried under reduced pressure to give 4-carbamoyl-4-(3-chloro-2-fluoro-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester as a white powder (1.30 g, 76%).

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layers were sequentially washed with H2O (×2) and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was triturated with H2O
  6. filtrationthe solid was collected by filtration
  7. washThe resulting solid was washed with Et2O
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-09c46e74b7d343f7938554a0b4959a9d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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