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 1747086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747086
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]

Komponenten

5

Edukt 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

Produkt 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-carboxamideAusbeute 51,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-df74ef206d854083be6781c5a1c25a55
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150541B2

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