Formaldehyde → 3-(5-Chlorothiophene-2-carbonyl)oxazolidine-5-carboxylic acid

HRID 602327

反応式

HRID 602327 の反応式
C=O.[CH2:3]([NH2:9])[CH:4]([OH:8])[C:5]([OH:7])=[O:6].[Cl:10][C:11]1[S:15][C:14]([C:16](Cl)=[O:17])=[CH:13][CH:12]=1.[C:19](=O)([O-])O.[Na+]>[OH-].[Na+].CC(C)=O.O>[Cl:10][C:11]1[S:15][C:14]([C:16]([N:9]2[CH2:3][CH:4]([C:5]([OH:7])=[O:6])[O:8][CH2:19]2)=[O:17])=[CH:13][CH:12]=1

参加物

8

反応物 4

HCID 712FormaldehydeHCID 11267IsoserineHCID 516892Sodium BicarbonateHCID 5892235-Chlorothiophene-2-carbonyl Chloride

生成物 1

HCID 586912493-(5-Chlorothiophene-2-carbonyl)oxazolidine-5-carboxylic acid

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

4.1 1.48 ml (19.9 mmol) of 37% aqueous formaldehyde solution are added to a solution of 2.00 g (19.0 mmol) of DL-isoserine in 10 ml of 1N aqueous sodium hydroxide solution. The resultant solution is left at 5° C. for 18 hours. A solution of 3.46 g (19.1 mmol) of 5-chlorothiophenecarbonyl chloride in 10 ml of acetone is added dropwise to this solution at an internal temperature of 0-5° C. During the dropwise addition, the pH is held at a value above 7 by addition of solid sodium hydrogencarbonate. When the addition is complete, the mixture is allowed to warm to room temperature, water is added, and the mixture is extracted with tert-butyl methyl ether The aqueous phase is acidified using 1N HCl and extracted with tert-butyl methyl ether. This organic phase is dried over sodium sulfate and evaporated, giving 3-(5-chlorothiophene-2-carbonyl)oxazolidine-5-carboxylic acid as a colourless solid; ESI 262.

後処理

  1. additionDuring the dropwise addition
  2. additionWhen the addition
  3. extractionthe mixture is extracted with tert-butyl methyl ether The aqueous phase
  4. extractionextracted with tert-butyl methyl ether
  5. dry with materialThis organic phase is dried over sodium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-f16f5ab193984ffc9ac0fa8a035495f7
出典データセット
uspto-grants-2011_03
特許番号
US07906516B2

関連ノート

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