Ammonium Chloride → HCID 58495248, compound

HRID 516238Notes

Reaction equation

HRID 516238 reaction equation
O[CH2:2][CH2:3][C:4]1[C:13]([CH3:14])=[C:12]2[C:7]([CH2:8][CH2:9][C:10](=[O:15])[NH:11]2)=[CH:6][C:5]=1[CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].CS(Cl)(=O)=O.CC(C)([O-])C.[K+].[Cl-].[NH4+]>C1COCC1.C(N(CC)CC)C>[CH3:14][C:13]1[C:4]2[CH2:3][CH2:2][N:18]([C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[CH2:17][CH2:16][C:5]=2[CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 58495252HCID 58495252, compound

Product 1

HCID 58495248HCID 58495248, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 1.793 g of t-butyl {2-[7-(2-hydroxyethyl)-8-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]ethyl}carbamate in 30 ml of THF were added 0.48 ml of methanesulfonyl chloride and 1.5 ml of triethylamine under ice-cooling, followed by stirring for 30 minutes. To the reaction mixture was added portionwise 1.8 g of potassium t-butoxide under ice-cooling, followed by stirring for 1.5 hours. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with EtOAc. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 1.06 g of t-butyl 11-methyl-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a white foamed substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring for 1.5 hours
  4. extractionfollowed by extraction with EtOAc
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-6ff54f14169e4f94b580837437173b60
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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