Water → ethyl 8-[(2-fluorobenzyl)oxy]-3-{[(1R)-2-hydroxy-1-phenylethyl]carbamoyl}-2-methylimidazo[1,2-a]pyridine-6-carboxylate

HRID 64460

Reaktionsgleichung

Reaktionsgleichung von HRID 64460
[Si]([O:8][CH2:9][C@H:10]([NH:17][C:18]([C:20]1[N:24]2[CH:25]=[C:26]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:27]=[C:28]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[F:37])[C:23]2=[N:22][C:21]=1[CH3:43])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O.C(OCC)(=O)C>C1COCC1>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[CH2:30][O:29][C:28]1[C:23]2[N:24]([C:20]([C:18](=[O:19])[NH:17][C@H:10]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:9][OH:8])=[C:21]([CH3:43])[N:22]=2)[CH:25]=[C:26]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 86713476ethyl 3-{[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]carbamoyl}-8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-6-carboxylate

Produkt 1

HCID 86713475ethyl 8-[(2-fluorobenzyl)oxy]-3-{[(1R)-2-hydroxy-1-phenylethyl]carbamoyl}-2-methylimidazo[1,2-a]pyridine-6-carboxylateAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 370 mg of ethyl 3-{[(1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl]carbamoyl}-8-[(2-fluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-6-carboxylate in 12 ml of THF was added 1.22 ml of a 1 M tetrabutylammonium fluoride/THF solution, followed by stirring for 30 minutes. To the reaction mixture were added water and ethyl acetate to carry out a layer separation operation. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 220 mg of ethyl 8-[(2-fluorobenzyl)oxy]-3-{[(1R)-2-hydroxy-1-phenylethyl]carbamoyl}-2-methylimidazo[1,2-a]pyridine-6-carboxylate.

Aufarbeitung

  1. customa layer separation operation
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aefaee30804b41c79e1934222da9d026
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447090B2

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