Water → HCID 118045462, compound

HRID 596015Notes

Reaction equation

HRID 596015 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][S:11](=[O:14])[N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[C:6]([F:8])[CH:7]=1.[OH2:22]>C(#N)C.CCOC(C)=O.O.[Ru](Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:13][O:12][S:11](=[O:22])(=[O:14])[N:10]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 2

HCID 962WaterHCID 118047004HCID 118047004, compound

Product 1

HCID 118045462HCID 118045462, compound

Reagents, catalysts & solvents 3

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice water cooled solution of (4S)-tert-butyl 4-(3-bromo-5-fluorophenyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide (34.6 g, 91 mmol) in acetonitrile (420 mL) under stirring was added NalO4 (29.2 g, 137 mmol), and ruthenium trichloride hydrate (0.359 g, 1.729 mmol), followed by water (320 ml). The reaction mixture was stirred at 0° C. for 2 hours. The mixture was diluted with EtOAc (500 ml), washed with brine (200 ml) twice, dried over Na2SO4, filtered and concentrated to afford the crude product, which was used directly at the next step. 40.3 grams of the crude product was obtained. LC-MS: (MW+Na): 419.9 m/z at 1.01 min.

Workup

  1. washwashed with brine (200 ml) twice
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the crude product, which

Sources & evidence

ORD record
ord-a9311b6cd95c49d0a27d34ee2b5cb45d
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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