HCID 86635614, compound → HCID 57948942, compound

HRID 1992287Notes

Reaction equation

HRID 1992287 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]([NH:17][S@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([CH3:16])[CH2:9][C:10](N(OC)C)=[O:11])[CH:5]=[CH:6][CH:7]=1.[CH3:24][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]([NH:17][S@@:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[O:19])([CH3:16])[CH2:9][C:10](=[O:11])[CH3:24])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 86635614HCID 86635614, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 57948942HCID 57948942, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of (S)-3-(3-bromo-phenyl)-N-methoxy-N-methyl-3-(R)-(2-methyl-propane-2-sulfinylamino)-butyramide (1.5 g, 3.7 mmoles; 1.0 equiv) in THF (53 mL) is added methylmagnesium bromide (6.2 mL, 18.5 mmoles, 5.0 equiv) and the reaction is allowed to warmed to ambient temperature. After 1 h, the reaction is cooled to −78° C. and quenched with saturated aqueous ammonium chloride. The mixture is diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (>95% yield): MS (m/z) 360, 362 (M+1)

Workup

  1. temperaturethe reaction is cooled to −78° C.
  2. customquenched with saturated aqueous ammonium chloride
  3. additionThe mixture is diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4950956ba03f43259902e5c9ac424e65
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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