Trifluoroacetic acid → HCID 59398317, compound

HRID 39897Notes

Reaction equation

HRID 39897 reaction equation
C(OC([N:8]([CH2:35][C:36]1[CH:45]=[CH:44][C:39]2[O:40][CH2:41][CH2:42][O:43][C:38]=2[CH:37]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[C:22]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]2=[O:34])[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:40]1[C:39]2[CH:44]=[CH:45][C:36]([CH2:35][NH:8][CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]4[C:26]5[C:21](=[C:22]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][C:18]4=[O:34])[CH2:13][CH2:14]3)=[CH:37][C:38]=2[O:43][CH2:42][CH2:41]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398057HCID 59398057, compound

Product 1

HCID 59398317HCID 59398317, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 83 mg of ethyl (1-(2-(4-((tert-butoxycarbonyl) (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetate, 2 mL of trifluoroacetic acid was added and stirred at room temperature for 6 hours. After the solvent was removed under reduced pressure and the residue was alkalized by aqueous saturated sodium hydrogen carbonate solution, it was extracted with ethyl acetate. The organic layer was washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 48 mg of ethyl (1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinolin-5-yloxy)acetate as a white solid.

Workup

  1. additionwas added
  2. customAfter the solvent was removed under reduced pressure
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed sequentially with water and aqueous saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d2a928ed78774ae6bb58ef41a18251ad
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…