Trifluoroacetic acid → 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

HRID 1965289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1965289
C([SiH](CC)CC)C.O[C:9]1([C:25]2[C:35]([OH:36])=[CH:34][C:28]3[N:29]([CH3:33])[CH2:30][CH2:31][O:32][C:27]=3[CH:26]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][O:20]2)[C:10]1=[O:24].[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40]>ClCCl>[F:37][C:38]([F:43])([F:42])[C:39]([OH:41])=[O:40].[OH:36][C:35]1[C:25]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C@H:19]3[CH2:23][CH2:22][CH2:21][O:20]3)[C:10]2=[O:24])=[CH:26][C:27]2[O:32][CH2:31][CH2:30][N:29]([CH3:33])[C:28]=2[CH:34]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 685987153-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one

Produkt 1

HCID 685974793-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a cooled (0° C.) solution of triethylsilane (1.3 mL, 8.2 mmol) in trifluoroacetic acid (8 mL) was added dropwise a solution of 3-hydroxy-3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one (1.04 g, 2.62 mmol) in dichloromethane (3 mL). The resulting solution was warmed to reflux and stirred under nitrogen for 90 min. Once cooled, the solvent was removed under reduced pressure to afford 3-(6-hydroxy-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-7-yl)-1-[(2R)-tetrahydrofuran-2-ylmethyl]-1,3-dihydro-2H-indol-2-one trifluoroacetate as a light brown foam: MS (ES+) m/z 381.0 (M+1).

Aufarbeitung

  1. temperatureThe resulting solution was warmed
  2. temperatureto reflux
  3. temperatureOnce cooled
  4. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-be28d39b46994530900762713b5d100a
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415370B2

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