Sulfuric Acid → 4-(Methylsulfonyl)phenol

HRID 2070229ノート

反応式

HRID 2070229 の反応式
[CH3:1][CH:2]([CH2:4][C@H:5]([CH2:10][NH2:11])[CH2:6][C:7]([OH:9])=[O:8])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:18][CH:19]([CH3:39])[C:20]([O:22][CH2:23][CH2:24][O:25][C:26]([O:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1)=[O:27])=[O:21].S(=O)(=O)(O)O>C(#N)C.COC(C)(C)C.O>[CH3:3][CH:2]([CH3:1])[CH2:4][C@H:5]([CH2:10][NH:11][C:26]([O:25][CH2:24][CH2:23][O:22][C:20](=[O:21])[CH:19]([CH3:18])[CH3:39])=[O:27])[CH2:6][C:7]([OH:9])=[O:8].[CH3:38][S:35]([C:32]1[CH:33]=[CH:34][C:29]([OH:28])=[CH:30][CH:31]=1)(=[O:36])=[O:37]

参加物

9

反応物 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 5486971PregabalinHCID 67352456[4-(Methylsulfonyl)phenoxycarbonyloxy]ethyl 2-methylpropanoate

生成物 2

HCID 1233504-(Methylsulfonyl)phenolHCID 86640714(3S)-5-Methyl-3-({[(2-methylpropanoyloxy)ethoxy]carbonylamino}methyl)hexanoic Acid

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

Pregabalin (0.95 g) and water (25 mL) were charged to a vessel at room temperature. Potassium carbonate (0.8 g) was added in one portion and the mixture was stirred at room temperature for 5 minutes. A solution of [4-(methylsulfonyl)phenoxycarbonyloxy]ethyl 2-methylpropanoate D3 (1.6 g) in acetonitrile (25 mL) was added. After 6 hours, tert-butyl methyl ether (50 mL) was added and the reaction mixture was cooled to 5-10° C. A solution of 5% aqueous sulfuric acid was added to adjust the pH to approximately 3. The mixture was then warmed to room temperature and stirred for 10 minutes. The organic layer was washed with water (3×10 mL) and evaporated to yield the title compound E1 as an orange oil with 4-(methylsulfonyl)phenol impurity. The crude product was purified by silica gel chromatography using ethyl acetate and hexane (4:6) to provide 1 g of the title compound E1 as a viscous oil.

後処理

  1. waitAfter 6 hours
  2. temperaturethe reaction mixture was cooled to 5-10° C
  3. temperatureThe mixture was then warmed to room temperature
  4. stirringstirred for 10 minutes
  5. washThe organic layer was washed with water (3×10 mL)
  6. customevaporated

出典と根拠

ORDレコード
ord-fd5b76c55e5048b398d66d9b497510b7
出典データセット
uspto-grants-2012_10
特許番号
US08299291B2

反応ノート

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