Tert-Butanesulfinamide → (+/-)-N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamide

HRID 404849Notes

Reaction equation

HRID 404849 reaction equation
[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][C:24]([S:27]([NH2:29])=[O:28])([CH3:26])[CH3:25]>C1COCC1.[Cl-].[Na+].O.CCOC(C)=O>[CH2:1]([C:8]1[O:12][C:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:10][C:9]=1[CH:21]=[N:29][S:27]([C:24]([CH3:26])([CH3:25])[CH3:23])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 866938955-Benzyl-2-(2,5-difluorophenyl)oxazole-4-carbaldehyde

Product 1

HCID 67451222(+/-)-N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 5-benzyl-2-(2,5-difluorophenyl)oxazole-4-carbaldehyde (898 mg, 3.0 mmol) in THF (30.0 mL) was added (±)-2-methylpropane-2-sulfinamide (364 mg, 3.0 mmol), and Ti(OEt)4 (1.37 mL, 6.6 mmol). The reaction mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with brine (30 mL) and EtOAc (60 mL) followed by addition of Celite®. Then, the mixture was vigorously stirred for 1 h, and filtered. The filtrate was extracted by EtOAc. The organic layers was washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product (770 mg, 64%) was purified by automatic column chromatography to yield (±)—N-((5-benzyl-2-(2,5-difluorophenyl)oxazol-4-yl)methylene)-2-methylpropane-2-sulfinamide as pale yellow solid. LC/MS (uplc): MH+ 403.0, 1.21 min.

Workup

  1. additionfollowed by addition of Celite®
  2. stirringThen, the mixture was vigorously stirred for 1 h
  3. filtrationfiltered
  4. extractionThe filtrate was extracted by EtOAc
  5. washThe organic layers was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product (770 mg, 64%) was purified by automatic column chromatography

Sources & evidence

ORD record
ord-21ceffe65e544104a510217a93c07df7
Source dataset
uspto-grants-2014_06
Patent number
US08748626B2

Reaction notes

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