Trifluoroacetic acid → HCID 58376207, compound

HRID 1942458Notes

Reaction equation

HRID 1942458 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][CH2:8][CH2:9][N:10]1[C:15]2[CH:16]=[C:17]([C:21]([O:23][CH3:24])=[O:22])[C:18]([CH3:20])=[CH:19][C:14]=2[O:13][C:12]([CH3:26])([CH3:25])[C:11]1=[O:27])(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])O.[Na+]>>[CH3:24][O:23][C:21]([C:17]1[C:18]([CH3:20])=[CH:19][C:14]2[O:13][C:12]([CH3:25])([CH3:26])[C:11](=[O:27])[N:10]([CH2:9][CH2:8][CH2:7][C:6]([OH:28])=[O:5])[C:15]=2[CH:16]=1)=[O:22]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58375871HCID 58375871, compound

Product 1

HCID 58376207HCID 58376207, compound

Procedure

To methyl 4-(4-tert-butoxy-4-oxobutyl)-2,2,7-trimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (2.7 g) was added TFA (5 ml), and the mixture was stirred at room temperature for 2 hours. After the reaction was complete, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution, and the precipitated compound was extracted with ethyl acetate. The obtained ethyl acetate solution was washed with water and an aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The obtained residue (950 mg) was used in the subsequent reaction without further treatment.

Workup

  1. extractionthe precipitated compound was extracted with ethyl acetate
  2. washThe obtained ethyl acetate solution was washed with water
  3. dry with materialan aqueous sodium chloride solution, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained residue (950 mg) was used in the subsequent reaction without further treatment

Sources & evidence

ORD record
ord-f5277ec6570341f090e007f78d6af1b9
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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