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Hydrochloric Acid → (R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid

HRID 2175170
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인쇄 미리보기

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HRID 2175170 반응식
C([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([N:13]1[C:17]2=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=[C:16]2[N:15]([CH2:23][C:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][C:31]=3[CH3:33])[N:26]([CH3:34])[CH:25]=2)[C:14]1=[O:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[OH-].[Na+].Cl>CO>[CH3:34][N:26]1[C:27]2[C:32](=[C:31]([CH3:33])[CH:30]=[CH:29][CH:28]=2)[C:24]([CH2:23][N:15]2[C:16]3[C:17](=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=3)[N:13]([C@@H:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:5][C:4]([OH:36])=[O:3])[C:14]2=[O:35])=[CH:25]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58497460(R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

생성물 1

HCID 58497404(R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid수율 77.3%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To a solution of (R)-3-[1-(1,4-dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester (200 mg, 0.41 mmol) in MeOH (5 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then treated with 1N HCl and extracted with CH2Cl2 twice. The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 144 mg (76%) of the title compound as off-white solid. LCMS, M++1, m/z: 455.00.

후처리

  1. extractionextracted with CH2Cl2 twice
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

출처 및 근거

ORD 기록
ord-9ba96d6b36d54a8b93b867cf9a3ebf10
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09062056B2

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