Hydrochloric Acid → HCID 59397897, compound

HRID 2193303Notes

Reaction equation

HRID 2193303 reaction equation
CO.C([O:5][C:6](=[O:47])[CH2:7][O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=[O:46])[N:14]2[CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH:24]([N:27]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:28][C:29]2[CH:38]=[CH:37][C:32]3[O:33][CH2:34][CH2:35][O:36][C:31]=3[CH:30]=2)[CH2:23][CH2:22]1)C.[OH-].[Na+].Cl>O>[C:42]([O:41][C:39]([N:27]([CH2:28][C:29]1[CH:38]=[CH:37][C:32]2[O:33][CH2:34][CH2:35][O:36][C:31]=2[CH:30]=1)[CH:24]1[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][N:14]2[C:15]3[C:10](=[C:9]([O:8][CH2:7][C:6]([OH:47])=[O:5])[CH:18]=[CH:17][CH:16]=3)[CH:11]=[CH:12][C:13]2=[O:46])[CH2:26][CH2:25]1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 59398057HCID 59398057, compound

Product 1

HCID 59397897HCID 59397897, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixed solution of 5 mL methanol and 0.5 mL water containing 126 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, 0.2 mL of 5 mol/L aqueous sodium hydroxide solution was added and allowed to stand at room temperature for 2.5 hours. To the reaction mixture, water was added, and the solvent was removed under reduced pressure. After the residue thus obtained was acidified by adding 1 mol/L hydrochloric acid, it was extracted with chloroform. The extracts were washed with aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to give 90 mg of (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)acetic acid as a white foam.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customAfter the residue thus obtained
  3. extractionwas extracted with chloroform
  4. washThe extracts were washed with 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-e20b1119deec4e9daeb506ee6c367970
Source dataset
uspto-grants-2012_12
Patent number
US08329694B2

Reaction notes

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