Hydrochloric Acid → HCID 58495252, compound

HRID 516237Notes

Reaction equation

HRID 516237 reaction equation
COC[O:4][CH2:5][CH2:6][C:7]1[C:16]([CH3:17])=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[NH:14]2)=[CH:9][C:8]=1[CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].Cl.[OH-].[Na+].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>C1COCC1>[OH:4][CH2:5][CH2:6][C:7]1[C:16]([CH3:17])=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[NH:14]2)=[CH:9][C:8]=1[CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 58494595HCID 58494595, compound

Product 1

HCID 58495252HCID 58495252, compoundYield 123.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1.01 g of t-butyl (2-{7-[2-(methoxymethoxy)ethyl]-8-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl}ethyl)carbamate in 10 ml of THF was added 10 ml of 6 M hydrochloric acid, followed by stirring at 50° C. for 1 hour. The reaction mixture was alkalified by the addition of sodium hydroxide and then 675 mg of di-t-butyl dicarbonate was added thereto, followed by stirring at room temperature for 15 hours. The reaction mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain 1.105 g of t-butyl {2-[7-(2-hydroxyethyl)-8-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl]ethyl}carbamate as a white foamed substance.

Workup

  1. stirringby stirring at room temperature for 15 hours
  2. extractionThe reaction mixture was extracted with chloroform
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d654ac94c354f67884b8cd034ce53d3
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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