Hydrochloric Acid → HCID 68833714, compound

HRID 1986446Notes

Reaction equation

HRID 1986446 reaction equation
[NH2:1][C:2](=[O:34])[CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[C:8]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.FC(F)(F)C(O)=O.[ClH:42]>O1CCCC1.C(OCC)(=O)C>[ClH:42].[ClH:42].[NH2:20][CH2:19][C:9]1[C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[N:11][C:12]2[C:7]([C:8]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:6][C:5]([O:4][CH2:3][C:2]([NH2:1])=[O:34])=[CH:14][CH:13]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 86605634HCID 86605634, compound

Product 1

HCID 68833714HCID 68833714, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of tert-butyl [6-(2-amino-2-oxoethoxy)-2-isobutyl-4-phenylquinolin-3-yl]methylcarbamate (0.10 g, 0.21 mmol) in tetrahydrofuran (5 ml) was added trifluoroacetic acid (5 ml), and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was partitioned between ethyl acetate (50 ml) and 10% aqueous potassium carbonate solution (100 ml). The aqueous layer was separated and extracted twice with ethyl acetate-isopropanol (10:1, 25 ml). The organic layer and the extract were combined and washed with saturated brine (10 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give a colorless oil. The obtained colorless oil was dissolved in ethyl acetate (2 ml) and 4N solution of hydrogen chloride in ethyl acetate (1 ml) was added. The reaction mixture was concentrated and the obtained residue was crystallized from diisopropyl ether-methanol to give the title compound (0.062 g, yield 67%) as pale-yellow crystals.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (50 ml) and 10% aqueous potassium carbonate solution (100 ml)
  2. customThe aqueous layer was separated
  3. extractionextracted twice with ethyl acetate-isopropanol (10:1, 25 ml)
  4. washwashed with saturated brine (10 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customto give a colorless oil
  9. concentrationThe reaction mixture was concentrated
  10. customthe obtained residue was crystallized from diisopropyl ether-methanol

Sources & evidence

ORD record
ord-cf733887d2c6422b8f94c67fa7077632
Source dataset
uspto-grants-2009_06
Patent number
US07547710B2

Reaction notes

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