Hydrochloric Acid → 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-5-carboxylic acid

HRID 39863Notes

Reaction equation

HRID 39863 reaction equation
[C:1]([O:5][C:6]([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[CH:25]=[C:24]([O:27][CH3:28])[CH:23]=[C:22]([C:29]([O:31]C)=[O:30])[C:21]=3[CH:20]=[CH:19][C:18]2=[O:33])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO.O1CCCC1.O>[C:1]([O:5][C:6]([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[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[CH:25]=[C:24]([O:27][CH3:28])[CH:23]=[C:22]([C:29]([OH:31])=[O:30])[C:21]=3[CH:20]=[CH:19][C:18]2=[O:33])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59398062HCID 59398062, compound

Product 1

HCID 593980221-(2-(4-((Tert-butoxycarbonyl) (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-5-carboxylic acidYield 121.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

466 mg 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-5-carboxylate was dissolved in a mixture of 7 mL of methanol, 5 mL of tetrahydrofuran and 3 mL of water. To this mixture, 0.77 mL of 5 mol/L sodium hydroxide was added and stirred at room temperature for 1 hour. To the reaction mixture, hydrochloric acid was added to make acidic, the resulting solid was filtered and dissolved in chloroform. The chloroform solution was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 553 mg of 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-5-carboxylic acid.

Workup

  1. filtrationthe resulting solid was filtered
  2. dissolutiondissolved in chloroform
  3. dry with materialThe chloroform solution was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b8a6b2b2fe2e410191ee8db5fd962ed4
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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