Ethyl Acetate → (3RS,4RS)-3-(2,4-dichlorophenyl)-N-{[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]methoxy}-2-{(1SR,2 SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide

HRID 1747086노트

반응식

HRID 1747086 반응식
C([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH2:11][O:12][NH:13][C:14]([CH:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19](=[O:26])[N:18]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]3[NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:17]2[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=2[Cl:45])=[O:15])[N:7]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CO>[Cl:45][C:39]1[CH:40]=[C:41]([Cl:44])[CH:42]=[CH:43][C:38]=1[CH:17]1[CH:16]([C:14]([NH:13][O:12][CH2:11][C:8]2[N:7]=[C:6]([CH2:5][OH:4])[O:10][N:9]=2)=[O:15])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](=[O:26])[N:18]1[CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH:28]1[NH:33][S:34]([CH3:37])(=[O:36])=[O:35]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 72303716(3-{[({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}-1,2,4-oxadiazol-5-yl)methyl acetate

생성물 1

HCID 72303442(3RS,4RS)-3-(2,4-dichlorophenyl)-N-{[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]methoxy}-2-{(1SR,2 SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide수율 51.8%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 323 mg of (3-{[({[(3RS,4RS)-3-(2,4-dichlorophenyl)-2-{(1SR,2SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl]carbonyl}amino)oxy]methyl}-1,2,4-oxadiazol-5-yl)methyl acetate in 6.5 ml of methanol was added 66 mg of potassium carbonate, followed by stirring at room temperature for 3 hours. To the reaction solution was added ethyl acetate, followed by washing with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol) and then recrystallized from ethyl acetate to obtain 157 mg of (3RS,4RS)-3-(2,4-dichlorophenyl)-N-{[5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl]methoxy}-2-{(1SR,2SR)-2-[(mesyl)amino]cyclohexyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxamide as a white crystal.

후처리

  1. washby washing with a saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol)
  5. customrecrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-df74ef206d854083be6781c5a1c25a55
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150541B2

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