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

HRID 1424295노트

반응식

HRID 1424295 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8bfcfc3724a84d40ade5b194a7e72403
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927577B2

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