Tetrahydrofuran → HCID 90192607, compound

HRID 923508Notes

Reaction equation

HRID 923508 reaction equation
[C:1]([C@:4]1([CH3:18])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])(=O)[NH2:2].C1COCC1.C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>O>[C:1]([C@:4]1([CH3:18])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[N:5]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])#[N:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 129386929HCID 129386929, compound

Product 1

HCID 90192607HCID 90192607, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen gas flow, to a mixture of 11.0 g of tert-butyl (4S)-4-carbamoyl-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate and 170 ml of THF were added dropwise 11.0 ml of triethylamine and 8.0 ml of trifluoroacetic anhydride under ice-cooling, followed by warming to room temperature and stirring for 30 minutes. The reaction mixture was added to water, followed by extraction with ethyl acetate. The organic layer was washed with a 10% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 8.22 g of tert-butyl (4R)-4-cyano-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a 10% aqueous citric acid solution
  4. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-56b9178fe6e54fb2bd4c08928b3fbddb
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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