Cyanuric chloride → HCID 118045222, compound

HRID 595979Notes

Reaction equation

HRID 595979 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[N:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=[C:6]([CH2:8]O)[CH:7]=1.[Cl:24]C1N=C(Cl)N=C(Cl)N=1>CS(C)=O.CCOC(C)=O>[Cl:24][CH2:8][C:6]1[CH:5]=[C:4]([C@H:10]2[CH2:14][O:13][C:12]([CH3:16])([CH3:15])[N:11]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 118046478HCID 118046478, compound

Product 1

HCID 118045222HCID 118045222, compoundYield 157.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-tert-butyl 4-(3-fluoro-5-(hydroxymethyl)phenyl)-2,2-dimethyloxazolidine-3-carboxylate (330 mg, 1.014 mmol) in anhydrous DMSO (2. 028 mL) was added 2,4,6-trichloro-1,3,5-triazine (112 mg, 0.609 mmol) portionwise. The mixture was stirred at room temperature for 30 min. The mixture was diluted with EtOAc, and separated. The organic phase was washed with H2O (5×30 mL), dried over anhydrous Na2SO4, filtered off and concentrated under reduced pressure. The residue was purified with flash chromatography eluting with 0-100% EtOAc/heptane to provide (S)-tert-butyl 4-(3-(chloromethyl)-5-fluorophenyl)-2,2-dimethyloxazolidine-3-carboxylate (329 mg, 94%). LCMS (m/z): 288.1 (MH+-56), 1.12 min.

Workup

  1. customseparated
  2. washThe organic phase was washed with H2O (5×30 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with flash chromatography
  7. washeluting with 0-100% EtOAc/heptane

Sources & evidence

ORD record
ord-bde2b671353d4702b60208e7d1ec827a
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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