Water → HCID 57815438, compound

HRID 385580Notes

Reaction equation

HRID 385580 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([CH2:12][N:13]([CH:21]3[CH2:26][CH2:25][N:24](C(=O)C(F)(F)F)[CH2:23][CH2:22]3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].O.C(=O)([O-])O.[Na+]>CO.C(Cl)(Cl)Cl>[O:1]=[C:2]1[NH:11][C:10]2[N:9]=[C:8]([CH2:12][N:13]([CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 962Water2×HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57815387HCID 57815387, compound

Product 1

HCID 57815438HCID 57815438, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 0.30 g of tert-butyl ((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)methyl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate in 12 mL of methanol, 0.10 g of potassium carbonate and 3 mL of water were added, and the mixture was stirred at room temperature for 7 hours 30 minutes. To the reaction mixture, water, a saturated aqueous sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, and the aqueous layer was added with sodium chloride and extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.24 g of tert-butyl ((7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)methyl)(piperidin-4-yl)carbamate as a colorless foam.

Workup

  1. customthe organic layer was separated
  2. additionthe aqueous layer was added with sodium chloride
  3. extractionextracted with chloroform
  4. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f6b5329475cb4ab7b59375742412ccb8
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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