Hydrogen Peroxide → (2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)pentanoic acid

HRID 1892150ノート

反応式

HRID 1892150 の反応式
[CH:1]([O:3][C@H:4]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[C:31]([F:36])[CH:30]=2)=[CH:25][CH:24]=1)[C@@H:5]([CH:19]=[O:20])[CH2:6][CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])=[O:2].P([O-])(O)(O)=[O:38].[Na+].OO.Cl([O-])=O.[Na+]>C(#N)C.O>[F:35][C:33]1[CH:34]=[C:29]([C:26]2[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][C@@H:4]([O:3][CH:1]=[O:2])[C@H:5]([CH2:6][CH2:7][N:8]3[C:9](=[O:18])[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:16]3=[O:17])[C:19]([OH:38])=[O:20])=[CH:28][CH:27]=2)[CH:30]=[C:31]([F:36])[CH:32]=1

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86640489(1R,2S)-1-[2-(3',5'-difluorobiphenyl-4-yl)ethyl]-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-formylbutyl formate

生成物 1

HCID 86640488(2S,3R)-5-(3',5'-difluorobiphenyl-4-yl)-2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-(formyloxy)pentanoic acid収率 96.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
0 °C

実験手順

The compound (0.12 g) obtained from step d was taken in acetonitrile (6 mL) and water (1 mL), to this solution sodiumdihydrogen phosphate (0.05 g) was added. Reaction mixture was cooled to 0° C. and hydrogen peroxide (0.5 mL) and sodium chlorite (0.15 g) were added. After stirring the reaction mixture for additional 1 hour, solvents were evaporated on rotaevaporator, the residue was taken into water and extracted with ethyl acetate. Organic layer was washed with water and brine solution and dried over anhydrous sodium sulphate. Solvent was evaporated under the reduced pressure, to get the title compound (0.12 g)

後処理

  1. customReaction mixture
  2. customsolvents were evaporated on rotaevaporator
  3. extractionextracted with ethyl acetate
  4. washOrganic layer was washed with water and brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customSolvent was evaporated under the reduced pressure

出典と根拠

ORDレコード
ord-6e380f31c8994a0fab80f5f2f21c2ed6
出典データセット
uspto-grants-2013_08
特許番号
US08507670B2

反応ノート

読み込み中…