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

HRID 403469

反応式

HRID 403469 の反応式
[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]

参加物

5

反応物 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

生成物 1

HCID 86679899tert-Butyl {4-[5-(trans-2-fluorocyclohexyloxy)-7-propoxyoxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenoxy}acetate収率 93.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24f43d1ec1624cc4a7a461ab0bc7b292
出典データセット
uspto-grants-2014_06
特許番号
US08748436B2

関連ノート

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