Water → HCID 86710238, compound

HRID 2405925Notes

Reaction equation

HRID 2405925 reaction equation
[CH3:1][C@@:2]([S:14]([CH3:17])(=[O:16])=[O:15])([CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]1)[C:3]([OH:5])=O.CN1CCOCC1.[O:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[O:31][NH2:32].O>C1COCC1>[CH3:1][C@@:2]([S:14]([CH3:17])(=[O:16])=[O:15])([CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([CH3:13])[CH:10]=[N:9]1)[C:3]([NH:32][O:31][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][O:25]1)=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 70817564HCID 70817564, compound

Product 1

HCID 86710238HCID 86710238, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)butanoic acid (20 mg, 0.077 mmol, 1 eq) and CDMT (17.6 mg, 0.10 mmol, 1.3 eq) in THF (1 mL) was added N-methylmorpholine (10.9 mg, 0.108 mmol, 0.0120 mL, 1.4 eq) and the reaction mixture was stirred at RT for one hour. O-Tetrahydro-2H-pyran-2-yl-hydroxylamine (9.00 mg, 0.077 mmol, 1 eq) was added to the reaction mixture which was stirred overnight at RT. Water was added and the organic phase was separated. The aqueous phase was extracted with Et2O. The organic phases were combined, dried over sodium sulfate, filtered and concentrated to give (2R)-2-methyl-4-(4-methyl-1H-pyrazol-1-yl)-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide, (19 mg, 68%).

Workup

  1. stirringwas stirred overnight at RT
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was extracted with Et2O
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-039f7dcb9a154a6eae6f0b74f338c364
Source dataset
uspto-grants-2014_08
Patent number
US08809333B2

Reaction notes

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