Trifluoroacetic acid → HCID 59398267, compound

HRID 39773Notes

Reaction equation

HRID 39773 reaction equation
C(OC([N:8]([CH2:34][C:35]1[CH:44]=[CH:43][C:38]2[O:39][CH2:40][CH2:41][O:42][C:37]=2[CH:36]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[CH:20]=[C:19]([C:29]([O:31][CH3:32])=[O:30])[C:18]2=[O:33])[CH2:11][CH2:10]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[O:39]1[C:38]2[CH:43]=[CH:44][C:35]([CH2:34][NH:8][CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=5)[CH:20]=[C:19]([C:29]([O:31][CH3:32])=[O:30])[C:18]4=[O:33])[CH2:13][CH2:14]3)=[CH:36][C:37]=2[O:42][CH2:41][CH2:40]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59398102Methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 59398267HCID 59398267, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 2 mL of a chloroform solution containing 0.31 g of methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, 1 mL of trifluoroacetic acid was added and stirred for 3 hours. The solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate were added. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and extracts were combined, washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 0.22 g of methyl 1-(2-(4-((2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-3-carboxylate as a colorless oil.

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure, and aqueous saturated sodium hydrogen carbonate solution and ethyl acetate
  3. additionwere added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted twice with ethyl acetate
  6. washwashed with aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b70125671e5a49f6ab3df8cae022ff27
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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