Sodium Hydroxide → HCID 59398431, compound

HRID 39807Notes

Reaction equation

HRID 39807 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[C:24]([CH3:33])=[CH:23][C:22]4=[O:34])[CH2:15][CH:14]3[C:35]([O:37]CC)=[O:36])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+]>CO>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([CH2:11][CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[C:30]5[C:25](=[CH:26][CH:27]=[C:28]([O:31][CH3:32])[CH:29]=5)[C:24]([CH3:33])=[CH:23][C:22]4=[O:34])[CH2:15][CH:14]3[C:35]([OH:37])=[O:36])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59398294HCID 59398294, compound

Product 1

HCID 59398431HCID 59398431, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 3.3 mL of a 90% aqueous methanol solution containing 58 mg of ethyl 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylate, 22 mg of sodium hydroxide was added and stirred at room temperature for 30 min. Further, 66 mg of sodium hydroxide and 1.1 mL of a 90% aqueous methanol solution were added and stirred at room temperature for 6 hours. After the solvent was removed under reduced pressure, water was added, and adjusted to pH 1 with 6.0 mol/L hydrochloric acid, thereafter ethanol was added and adjusted to pH 6.5 with aqueous saturated sodium hydrogen carbonate solution and 1.0 mol/L hydrochloric acid. The resulting solid was filtered to give 35 mg of 1-(2-(2,3-dihydro-1,4-benzodioxin-6-yl)ethyl)-4-(2-(7-methoxy-4-methyl-2-oxoquinolin-1(2H)-yl)ethyl)piperazine-2-carboxylic acid as a white solid.

Workup

  1. additionwas added
  2. stirringstirred at room temperature for 6 hours
  3. customAfter the solvent was removed under reduced pressure, water
  4. additionwas added
  5. additionethanol was added
  6. filtrationThe resulting solid was filtered

Sources & evidence

ORD record
ord-5397322f6e3841b8ba817b680c164944
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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