Hydrochloric Acid → HCID 58032146, compound

HRID 2167267Notes

Reaction equation

HRID 2167267 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([O:16]CC)=[O:15])=[CH:11][CH:12]=2)[C@@H:7]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[CH:22][CH:21]=2)[CH2:6][C@@H:5]1[CH3:32])(=[O:3])[CH3:2].[OH-].[Na+].Cl>C(O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([OH:16])=[O:15])=[CH:11][CH:12]=2)[CH:7]([O:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)=[CH:24][CH:25]=2)[CH2:6][CH:5]1[CH3:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66625363HCID 66625363, compound

Product 1

HCID 58032146HCID 58032146, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

[Step 7] 59.4 mg of ethyl (2S,4S)-1-acetyl-2-methyl-4-(4-morpholinophenoxy)-1,2,3,4-tetrahydroquinoline-6-carboxylate was dissolved in 1 mL of ethanol, and 163 μL of 4 N sodium hydroxide was added to the solution. The mixture was stirred for 4 hours at room temperature. After completion of the reaction, the reaction liquid was adjusted to pH 7 with 1 N hydrochloric acid, and then was extracted three times with chloroform-methanol. The extraction product was dehydrated over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform:methanol=10:1), and thus 51.7 mg (93.3%, cis:trans=14:1) of the title compound was obtained as a pale peach-colored amorphous substance.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. extractionwas extracted three times with chloroform-methanol
  4. concentrationwas concentrated under reduced pressure
  5. customThe resulting residue was purified
  6. customwas obtained as a pale peach-colored amorphous substance

Sources & evidence

ORD record
ord-5a2b220701cd401dbc2f1e3c886d5a73
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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