Ammonium Chloride → HCID 66818142, compound

HRID 1754981Notes

Reaction equation

HRID 1754981 reaction equation
O[Li].O.[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:32](=[O:34])[NH2:33])([NH:17][C:18]([CH:20]2[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:22][CH2:21]2)=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[Cl-].[NH4+]>C(O)C>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14]2([N:17]=[C:18]([CH:20]3[CH2:25][CH2:24][CH:23]([CH2:26][CH2:27][C:28]([F:31])([F:30])[F:29])[CH2:22][CH2:21]3)[NH:33][C:32]2=[O:34])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 168937Lithium hydroxide, monohydrateHCID 66817865HCID 66817865, compound

Product 1

HCID 66818142HCID 66818142, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

LiOH.H2O (1.55 g, 36.9 mmol) was added to a solution of 4-carbamoyl-4-{[4-(3,3,3-trifluoro-propyl)-cyclohexanecarbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (5.53 g, 12.3 mmol) in ethanol (123 mL), and the mixture was stirred at 85° C. for two hours. A 50% saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by reprecipitation with hexane-ethyl acetate=3:1 to give 4-oxo-2-[4-(3,3,3-trifluoro-propyl)-cyclohexyl]-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (4.88 g, 92%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was then dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by reprecipitation with hexane-ethyl acetate=3:1

Sources & evidence

ORD record
ord-22376a91e276470bb216fac534db602d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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