Hydrochloric Acid → HCID 67953856, compound

HRID 469717Notes

Reaction equation

HRID 469717 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.Br[CH2:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH2:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:12])[O:7][N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 67457204HCID 67457204, compound

Product 1

HCID 67953856HCID 67953856, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-pyrrolidine-2-carboxylic acid (3-tert-butyl-isoxazol-5-yl)-amide; hydrochloride (0.2 g; 0.731 mmol) in N,N-dimethylformamide (4 mL) is added bromomethyl-cyclohexane (0.153 mL; 1.097 mmol), potassium iodide (0.032 mg, 0.197 mmoL), and potassium carbonate (0.505 g; 3.655 mmol). The mixture heated at 60° C. for 7 days. After this time, the mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organics are washed with water, 1N hydrochloric acid and brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude material is purified by preparative reverse phase HPLC to afford title compound. ESI m/z 334 [M+H]+

Workup

  1. temperatureAfter this time, the mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organics are washed with water, 1N hydrochloric acid and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-eac05f95cc63454c97619cac04f73429
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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