Hydrochloric Acid → 3-(4-((3,3-Dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzamido)propanoic acid

HRID 2281166Notes

Reaction equation

HRID 2281166 reaction equation
[CH3:1][C:2]1([CH3:34])[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][CH:30]=[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([CH3:34])[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][CH:30]=[CH:29][CH:28]=3)[C:7]2[CH:22]=[CH:21][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:12])=[CH:9][CH:8]=2)[CH2:3]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71239304Ethyl 3-(4-((3,3-dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzamido)propanoate

Product 1

HCID 712394183-(4-((3,3-Dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzamido)propanoic acidYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a flask containing ethyl 3-(4-((3,3-dimethylcyclobutyl)(quinolin-3-ylamino)methyl)benzamido)propanoate (11.9 mg, 0.0650 mmol) was added tetrahydrofuran (0.0650 mL), methanol (0.0650 mL), and 1 N sodium hydroxide (0.0650 mL, 0.0650 mmol). The reaction was stirred for 18 h at room temperature. The reaction was then diluted with ethyl acetate and water. 1 N hydrochloric acid (0.0650 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)(quinolin-3-ylamino)methyl)benzamido)propanoic acid (9.3 mg, 83% yield) as a solid. 1H NMR (400 MHz, CD3OD) δ: 8.50 (d, J=2.7 Hz, 1H), 8.45 (t, J=5.8 Hz, 1H), 7.81-7.70 (m, 3H), 7.61-7.52 (m, 2H), 7.52-7.41 (m, 1H), 7.41-7.21 (m, 2H), 6.93 (d, J=2.7 Hz, 1H), 4.39 (d, J=9.8 Hz, 1H), 3.69-3.55 (m, 2H), 2.71-2.51 (m, 3H), 2.11 (ddd, J=11.4, 7.8, 4.1 Hz, 1H), 1.85-1.70 (m, 2H), 1.57 (ddd, J=11.3, 7.8, 4.1 Hz, 1H), 1.18 (s, 3H), 1.13 (s, 3H). MS (M+1): 432.3.

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-a381beddceff42a7b0ca8dcfe1fba71c
Source dataset
uspto-grants-2015_09
Patent number
US09139538B2

Reaction notes

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