Sulfuric Acid → 4-(Methylsulfonyl)phenol

HRID 2070230ノート

反応式

HRID 2070230 の反応式
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.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>[CH3:18][CH:19]([CH3:39])[C:20]([O:22][CH2:23][CH2:24][O:25][C:26]([NH:1][CH2:2][CH:3]1[CH2:4][CH2:5][CH:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]1)=[O:27])=[O:21].[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 67352456[4-(Methylsulfonyl)phenoxycarbonyloxy]ethyl 2-methylpropanoateHCID 178511262HCID 178511262、化合物

生成物 2

HCID 1233504-(Methylsulfonyl)phenolHCID 672943074-({[(2-Methylpropanoyloxy)ethoxy]carbonylamino}methyl)cyclohexanecarboxylic 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

Trans-4-(Aminomethyl)-cyclohexanecarboxylic acid (0.94 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 as an orange oil with 4-(methylsulfonyl)phenol as an impurity. Tert-butyl methyl ether (10 mL) and methylcyclohexane (5 mL) were added and the mixture was heated at 50° C. for 10 minutes. The mixture was then cooled to 40° C. over a period of 2 hours. The crystallization solution was seeded with 4-({[(2-methylpropanoyloxy)ethoxy]carbonylamino}methyl)cyclohexanecarboxylic acid (10 mg) and then stirred for 2 hours. The white, thick slurry was filtered and dried under vacuum at room temperature to provide 1 g of the title compound E2.

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-2a61272f13eb4f86b2b7453c5a60f884
出典データセット
uspto-grants-2012_10
特許番号
US08299291B2

反応ノート

読み込み中…