Hydrochloric Acid → HCID 70864988, compound

HRID 336191Notes

Reaction equation

HRID 336191 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C@H:17]2[C:22](=[O:33])[NH:23][C:24]2[CH:28]=[C:27]([C:29]([CH3:32])([CH3:31])[CH3:30])[O:26][N:25]=2)=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1.C([O-])(O)=O.[Na+]>ClCCl.C(OCC)(=O)C>[C:29]([C:27]1[O:26][N:25]=[C:24]([NH:23][C:22]([C@@H:17]2[CH2:18][CH2:19][CH2:20][CH2:21][N:16]2[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])=[O:33])[CH:28]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 516892Sodium BicarbonateHCID 70865353HCID 70865353, compound

Product 1

HCID 70864988HCID 70864988, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[(S)-2-(5-tert-Butyl-isoxazol-3-ylcarbamoyl)-piperidine-1-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (655 mg; 1.413 mmol) in dichloromethane (100 mL) is added 4N hydrochloric acid in dioxane (1.25 mL; 5 mmol) and the reaction mixture is stirred at room temperature for 3 hours. More 4N hydrochloric acid in dioxane (1.25 mL; 5 mmol) is added and the stirring is continued for another 3 hours. After this time, the reaction mixture is concentrated to afford the product. The product is taken up in the mixture of ethyl acetate and saturated NaHCO3 aqueous solution to free base the product. The aqueous layer is extracted with ethyl acetate twice. The combined organics are washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound, m/z 364 [M+H+].

Workup

  1. waitthe stirring is continued for another 3 hours
  2. concentrationAfter this time, the reaction mixture is concentrated
  3. customto afford the product
  4. extractionThe aqueous layer is extracted with ethyl acetate twice
  5. washThe combined organics are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f0bf6ec8999c4fbea1b0af92ac6b5cf1
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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