Hydrochloric Acid → HCID 70865353, compound

HRID 336190Notes

Reaction equation

HRID 336190 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N(CC)C(C)C)(C)C.[C:29]([O:33][C:34]([N:36]1[CH2:41][CH2:40][N:39]([C:42](Cl)=[O:43])[CH2:38][CH2:37]1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>C1COCC1.C(OCC)(=O)C>[C:29]([O:33][C:34]([N:36]1[CH2:37][CH2:38][N:39]([C:42]([N:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]2[C:11](=[O:12])[NH:10][C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:9][N:8]=2)=[O:43])[CH2:40][CH2:41]1)=[O:35])([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 70864984HCID 70864984, compound

Product 1

HCID 70865353HCID 70865353, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-Piperidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl) amide; hydrochloride (675 mg; 2.345 mmol) in THF (18 mL) is added N,N-diisopropylethylamine (0.81 mL; 4.65 mmol) and 4-chlorocarbonyl-piperazine-1-carboxylic acid tert-butyl ester (609 mg; 2.45 mmol). The reaction mixture is left stirring at room temperature for 18 hours. After this time, the reaction mixture is diluted with ethyl acetate and washed with water then brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel using ethyl acetate/Hexanes provides the title compound, m/z 464 [M+H+].

Workup

  1. waitThe reaction mixture is left
  2. washwashed with water
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-4ea767e0bad745f6a46479b7ff52b573
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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