Triethylamine → 4-(4-(Benzyloxy)-2-oxopyridin-1(2h)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2h-pyran-2-yloxy)butanamide

HRID 84272Notes

Reaction equation

HRID 84272 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:25])([S:21]([CH3:24])(=[O:23])=[O:22])[C:18](O)=[O:19])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[O:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH:46]1[O:51][NH2:52]>C(Cl)Cl.O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][CH2:16][C:17]([CH3:25])([S:21]([CH3:24])(=[O:22])=[O:23])[C:18]([NH:52][O:51][CH:46]2[CH2:47][CH2:48][CH2:49][CH2:50][O:45]2)=[O:19])[C:11](=[O:26])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 67250346HCID 67250346, compound

Product 1

HCID 866719504-(4-(Benzyloxy)-2-oxopyridin-1(2h)-yl)-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2h-pyran-2-yloxy)butanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-[4-(benzyloxy)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)butanoic acid (670 mg, 1.77 mmol) in methylene chloride (18 mL) at ambient temperature was added 1,(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (474 mg, 2.47 mmol), 1-hydroxy benzotriazole monohydrate (487 mg, 3.18 mmol), triethylamine (443 uL, 3.18 mmol) and O-tetrahydro-2H-pyran-2-yl-hydroxylamine (310 mg, 2.65 mmol). The resulting mixture was stirred at ambient temperature overnight. The mixture was diluted with methylene chloride and water. The phases were separated and the aqueous layer was extracted with methylene chloride two times. The organic extracts were combined and dried over magnesium sulfate, filtered and concentrated to a crude residue. The crude residue was purified via silica gel chromatography eluting with methylene chloride and methanol. The fractions containing desired product were combined and concentrated to afford 4-[4-(benzyloxy)-2-oxopyridin-1(2H)-yl]-2-methyl-2-(methylsulfonyl)-N-(tetrahydro-2H-pyran-2-yloxy)butanamide as an oil. 536.3 mg

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with methylene chloride two times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a crude residue
  6. customThe crude residue was purified via silica gel chromatography
  7. washeluting with methylene chloride and methanol
  8. additionThe fractions containing desired product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-03054362e0384a9289384367268efbb4
Source dataset
uspto-grants-2014_09
Patent number
US08846933B2

Reaction notes

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