Sodium hydride → tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate

HRID 403469

Reaktionsgleichung

Reaktionsgleichung von HRID 403469
[F:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[OH:8].[H-].[Na+].[C:11]([O:15][C:16](=[O:44])[CH2:17][O:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([C:26]2[O:27][C:28]3[N:29]=[C:30](S(C)(=O)=O)[N:31]=[C:32]([O:35][CH2:36][CH2:37][CH3:38])[C:33]=3[N:34]=2)=[CH:21][C:20]=1[CH3:43])([CH3:14])([CH3:13])[CH3:12]>CN(C)C=O>[C:11]([O:15][C:16](=[O:44])[CH2:17][O:18][C:19]1[C:24]([CH3:25])=[CH:23][C:22]([C:26]2[O:27][C:28]3[N:29]=[C:30]([O:8][C@@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]4[F:1])[N:31]=[C:32]([O:35][CH2:36][CH2:37][CH3:38])[C:33]=3[N:34]=2)=[CH:21][C:20]=1[CH3:43])([CH3:12])([CH3:13])[CH3:14]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 12700773(1R,2R)-2-fluorocyclohexan-1-olHCID 86679896Tert-butyl [4-(5-methanesulfonyl-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethylphenoxy]acetate

Produkt 1

HCID 86679899tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetateAusbeute 93,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

26 mg of trans-2-fluoro-cyclohexanol were added under argon atmosphere at 0° C. to a suspension of 10 mg of sodium hydride (60% in mineral oil) in 2 ml of N,N-dimethylformamide. After 15 min a solution of 100 mg of [4-(5-methanesulfonyl-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 1 ml of N,N-dimethylformamide was slowly added. After 12 h at room temperature the mixture was quenched by the addition of water and extracted twice with ethyl acetate. The combined organic layers were dried and concentrated in vacuo. 101 mg of the title compound were obtained.

Aufarbeitung

  1. customAfter 12 h at room temperature the mixture was quenched by the addition of water
  2. extractionextracted twice with ethyl acetate
  3. customThe combined organic layers were dried
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-24f43d1ec1624cc4a7a461ab0bc7b292
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748436B2

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