Tetrahydrofuran → (2S,3R)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-(4-pyrimidin-5-ylphenyl)pentanoic acid

HRID 2410407ノート

反応式

HRID 2410407 の反応式
[OH:1][C@@H:2]1[C@H:6]([OH:7])[O:5][C@H:4]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:17]=[N:18][CH:19]=[N:20][CH:21]=3)=[CH:12][CH:11]=2)[C@@H:3]1[CH2:22][CH2:23][N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1.[O:35]1CCCC1.I([O-])(=O)(=O)=O.[Na+].[Mn]([O-])(=O)(=O)=O.[K+]>C(O)(C)(C)C>[CH:6]([O:5][C@H:4]([CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[N:20][CH:19]=[N:18][CH:17]=2)=[CH:14][CH:15]=1)[C@H:3]([CH2:22][CH2:23][N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1)[C:2]([OH:1])=[O:35])=[O:7]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 516875Potassium PermanganateHCID 23667635Sodium periodateHCID 67184114HCID 67184114、化合物

生成物 1

HCID 86700967(2S,3R)-3-(formyloxy)-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]-5-(4-pyrimidin-5-ylphenyl)pentanoic acid

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of the compound obtained from step m above (0.25 g) in tert-butanol: tetrahydrofuran (5 mL:5 mL) at 0° C., a solution of sodium metaperiodate (0.465 g in 5 mL of water) was added. The reaction mixture was stirred for 2 hours at the same temperature and potassium permanganate (0.017 g) was added at 0° C. After stirring the reaction mixture for an additional 6 hours at room temperature, the reaction mixture was evaporated on a rotary evaporator. The residue was taken into water and extracted with ethyl acetate. The organic layer was washed with water and brine solution and dried over anhydrous sodium sulphate. The solvent was evaporated under the reduced pressure to afford the title compound (0.25 g).

後処理

  1. additionwas added at 0° C
  2. customthe reaction mixture was evaporated on a rotary evaporator
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customThe solvent was evaporated under the reduced pressure

出典と根拠

ORDレコード
ord-5a317c3ea1b44f0f9fe7a2560034f9a9
出典データセット
uspto-grants-2014_08
特許番号
US08816073B2

反応ノート

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