Hydrochloric Acid → HCID 71239342, compound

HRID 1424294Notes

Reaction equation

HRID 1424294 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([F:34])=[CH:29][CH:28]=3)[C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1.O1CCCC1.[OH-].[Na+].Cl>C(OCC)(=O)C.O.CO>[CH3:1][C:2]1([CH3:35])[CH2:5][CH:4]([CH:6]([NH:23][C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][C:30]([F:34])=[CH:29][CH:28]=3)[C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12])=[CH:21][CH:22]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71239399HCID 71239399, compound

Product 1

HCID 71239342HCID 71239342, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing ethyl 3-(4-((3,3-dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino)methyl)benzamido)propanoate (7.4 mg, 0.0420 mmol) was added tetrahydrofuran (0.105 mL), methanol (0.105 mL), and 1 N sodium hydroxide (0.105 mL, 0.105 mmol). The reaction was stirred for 4.5 h at room temperature. The reaction was then diluted with ethyl acetate and water. 1 N hydrochloric acid (0.105 mL) was then added dropwise to bring the pH to 3. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to provide 3-(4-((3,3-dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino)methyl)benzamido)propanoic acid (6.7 mg, 99% yield) as a solid. 1H NMR (400 MHz, CD3OD, 6): 8.46 (d, J=2.7 Hz, 1H), 7.83-7.72 (m, 3H), 7.57-7.50 (m, 2H), 7.17-7.09 (m, 2H), 6.85 (d, J=2.7 Hz, 1H), 4.38 (d, J=9.8 Hz, 1H), 3.62 (t, J=6.9 Hz, 2H), 2.69-2.54 (m, 3H), 2.11 (ddd, J=11.4, 7.7, 4.2 Hz, 1H), 1.77 (ddd, J=11.2, 9.0, 2.6 Hz, 2H), 1.63-1.52 (m, 1H), 1.18 (s, 3H), 1.13 (s, 3H). (M+1): 450.3.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. dry with materialThe combined organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bc0632eb8eb34cc592e4731195e48084
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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