Acetone → HCID 59397872, compound

HRID 2193195Notes

Reaction equation

HRID 2193195 reaction equation
CC(C)=O.[C:5]([O:9][C:10]([N:12]([CH2:36][C:37]1[CH:46]=[CH:45][C:40]2[O:41][CH2:42][CH2:43][O:44][C:39]=2[CH:38]=1)[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([O:33]C)=[O:32])=[CH:23][C:22]2=[O:35])[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].[OH-].[Na+]>O>[C:5]([O:9][C:10]([N:12]([CH2:36][C:37]1[CH:46]=[CH:45][C:40]2[O:41][CH2:42][CH2:43][O:44][C:39]=2[CH:38]=1)[CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([OH:33])=[O:32])=[CH:23][C:22]2=[O:35])[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 59397905tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-methoxycarbonyl-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

Product 1

HCID 59397872HCID 59397872, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 11 mL of acetone solution containing 1.1g of methyl 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxylate, 2.2 mL of water solution containing 0.23 g of sodium hydroxide was added at room temperature, and stirred at 50° C. for 30 min. After cooled to the room temperature, the solvent was removed under reduced pressure, 40 mL of water was added, and adjusted to pH 4 with 2 mol/L hydrochloric acid. The resulting solid was filtered to afford 0.97 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-2-oxo-1,2-dihydroquinoline-4-carboxylic acid as a white solid.

Workup

  1. additionwas added at room temperature
  2. temperatureAfter cooled to the room temperature
  3. customthe solvent was removed under reduced pressure, 40 mL of water
  4. additionwas added
  5. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-bb52ccf53b4a455481d531c100789969
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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