Hydrogen Peroxide → (2-{3-Chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268577ノート

反応式

HRID 2268577 の反応式
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:34])[N:25]([CH2:31][CH:32]=[CH2:33])[CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.[OH:45]O.[OH-].[Na+]>>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([C:24](=[O:34])[N:25]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:31][CH2:32][CH2:33][OH:45])[CH:20]=[C:21]([Cl:23])[CH:22]=1)[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

参加物

5

反応物 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 18349220{2-[3-(Allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

生成物 1

HCID 54299674(2-{3-Chloro-5-[cyclopentyl-(3-hydroxy-propyl)-carbamoyl]-phenoxy}-ethyl)-pyridin-4-yl-carbamic acid tert-butyl ester

実験手順

To {2-[3-(allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester (0.11 g) was added 9-BBN (0.5M in THF, 2.2 ml) and the resulting solution stirred at room temperature under nitrogen for 20 h. A mixture of 28% aqueous hydrogen peroxide solution (1.8 ml) and 2M aqueous sodium hydroxide (0.9 ml) was added and the reaction mixture stirred at reflux for 2 h. The solvent was removed in vacuo and the residue purified by preparative hplc and the title compound (0.064 g) was obtained as a colourless gum by concentration of the required fraction under reduced pressure and drying by repetitive addition of acetonitrile and concentration under reduced pressure.

後処理

  1. additionwas added
  2. stirringthe reaction mixture stirred
  3. temperatureat reflux for 2 h
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by preparative hplc

出典と根拠

ORDレコード
ord-48b3b67fe6e94ece89c844e6001e708d
出典データセット
uspto-grants-2001_12
特許番号
US06326386B1

反応ノート

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