4-Methylmorpholine → HCID 86710233, compound

HRID 2405917Notes

Reaction equation

HRID 2405917 reaction equation
[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:21])([S:17]([CH3:20])(=[O:19])=[O:18])[C:14]([OH:16])=O)[CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.[O:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[O:35][NH2:36]>O>[CH:1]1([C:6]2[CH:7]=[N:8][N:9]([CH2:11][CH2:12][C@@:13]([CH3:21])([S:17]([CH3:20])(=[O:19])=[O:18])[C:14]([NH:36][O:35][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][O:29]3)=[O:16])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 70817619HCID 70817619, compound

Product 1

HCID 86710233HCID 86710233, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (100 mg, 0.318 mmol, 1 eq) and CDMT (73.2 mg, 0.413 mmol, 1.3 eq) were charged into a flask. The flask was flushed with nitrogen and then 2-MeTHF (5 mL) added. To this mixture was added N-methylmorpholine (50 uL, 0.445 mmol, 1.4 eq) and the reaction mixture was stirred at RT for one hour. O-Tetrahydro-2H-pyran-2-yl-hydroxylamine (49 mg, 0.413 mmol, 1.3 eq) was added and the reaction mixture was stirred overnight at RT. Water (25 mL) was added and the organic phase was separated. The aqueous phase was extracted with ethyl acetate (50 mL). The organic phases were combined, dried over sodium sulfate, filtered and concentrated to give (2R)-4-(4-cyclopentyl-1H-pyrazol-1-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (100 mg, 76% yield) which was used without further purification. LC-MS M+H+414.1.

Workup

  1. customThe flask was flushed with nitrogen
  2. addition2-MeTHF (5 mL) added
  3. stirringthe reaction mixture was stirred overnight at RT
  4. customthe organic phase was separated
  5. extractionThe aqueous phase was extracted with ethyl acetate (50 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e61e82f5e6504896a523925ed6d1aea4
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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