Citric Acid → (R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid

HRID 2175175노트

반응식

HRID 2175175 반응식
C([O:3][C:4](=[O:36])[CH2:5][C@@H:6]([N:13]1[C:21]2[CH:20]=[C:19]([CH3:22])[N:18]=[CH:17][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+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>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[CH:17]=[N:18][C:19]([CH3:22])=[CH:20][C: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 물질

5

반응물 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58497394(R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester

생성물 1

HCID 58497450(R)-3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid수율 89%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (R)-3-[3-(1,4-dimethyl-1H-indol-3-ylmethyl)-6-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]pyridin-1-yl]-3-phenyl-propionic acid ethyl ester (80 mg, 0.17 mmol) in MeOH (5 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction was then treated with 0.5N citric acid solution. The reaction mixture was extracted with CH2Cl2 twice. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 10:5 CH2Cl2:MeOH as an eluent to afford 67 mg (89%) of the title compound as a white floppy solid. LCMS, M++1, m/z: 456.15.

후처리

  1. extractionThe reaction mixture was extracted with CH2Cl2 twice
  2. dry with materialThe 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-a1ec4ed75c0447e79629ac05ba981a88
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062056B2

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