Hydrochloric Acid → 1-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336180Notes

Reaction equation

HRID 336180 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(N(CC)CC)C.[O:27]=[S:28]1(=[O:37])[CH2:33][CH2:32][N:31]([C:34](Cl)=[O:35])[CH2:30][CH2:29]1>C1COCC1.O>[C:1]([C:5]1[O:9][N:8]=[C:7]([NH:10][C:11]([CH:13]2[CH2:18][CH2:17][CH2:16][N:15]([C:34]([N:31]3[CH2:32][CH2:33][S:28](=[O:37])(=[O:27])[CH2:29][CH2:30]3)=[O:35])[CH2:14]2)=[O:12])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 216949071,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl chlorideHCID 58563805Piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Product 1

HCID 468720441-(1,1-Dioxo-1lambda6-thiomorpholine-4-carbonyl)-piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of piperidine-3-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide; hydrochloride (100 mg; 0.347 mmol) in anhydrous THF (1 mL) is added triethylamine (0.098 mL; 0.7 mmol) and 1,1-dioxo-1λ6-thiomorpholine-4-carbonyl chloride (71.15 mg; 0.36 mmol). The reaction mixture is left stirring at room temperature overnight. The reaction mixture is diluted with water and extracted with ethyl acetate 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo.

Workup

  1. waitThe reaction mixture is left
  2. extractionextracted with ethyl acetate 3 times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17bba68d3261432b941d55a2e4b12c1a
Source dataset
uspto-grants-2014_11
Patent number
US08889670B2

Reaction notes

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