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Acetone → (S)-tert-butyl (1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)quinolin-3-yl)-ethyl)carbamate

HRID 1019798
Notes
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Reaction equation

HRID 1019798 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18][CH3:19])=[N:9]2)=[CH:4][CH:3]=1.CC(C)=[O:32].C[N+]1([O-])CCOCC1.[OH2:42]>O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C@@H:20]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:21])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:19])(=[O:32])=[O:42])=[N:9]2)=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 86698501(S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)quinolin-3-yl)ethyl)carbamate

Product 1

HCID 57707808(S)-tert-butyl (1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)quinolin-3-yl)-ethyl)carbamateYield 99%

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst2×

Procedure

Under an N2 atmosphere, (S)-tert-butyl (1-(7-fluoro-2-(2-(methylthio)phenyl)-quinolin-3-yl)ethyl)carbamate (412 mg, 999 μmol) was dissolved in acetone (3.00 ml, 40.8 mmol) and water (3 mL), and NMO (351 mg, 3.00 mmol) was added followed by OsO4 (12.7 mg, 0.05 mmol). The reaction was allowed to stir at rt overnight. LC-MS showed the reaction not to be complete. The reaction was treated with OsO4 (12.7 mg, 0.05 mmol) again and stirred overnight. LC-MS showed only a trace of the starting reagent. The reaction was quenched by the addition of 5 mL of a saturated sodium thiosulfate solution. The reaction was diluted with EtOAc and washed with 5% Na2CO3. The organic layer was then washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified eluting with 30% to 60% EtOAc in hexanes to provide a white solid (S)-tert-butyl (1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)quinolin-3-yl)-ethyl)carbamate (440 mg, 99%). Mass Spectrum (ESI) m/e=445 (M+1).

Workup

  1. customthe reaction not
  2. stirringstirred overnight
  3. customThe reaction was quenched by the addition of 5 mL of a saturated sodium thiosulfate solution
  4. additionThe reaction was diluted with EtOAc
  5. washwashed with 5% Na2CO3
  6. washThe organic layer was then washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified
  11. washeluting with 30% to 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-a9fd8a06456a4282a24b77e9aab34d20
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716290B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes