Hydrochloric Acid → (4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

HRID 1388125ノート

反応式

HRID 1388125 の反応式
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7]1.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:21][CH2:22][C:23](Cl)=[O:24].[C:26]([O-:34])(=[S:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[K+].Cl>O>[C:26]([S:33][CH2:21][CH2:22][C:23]([N:10]1[C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][S:7][CH:6]1[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:24])(=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 84944Propanoyl chloride, 3-bromo-HCID 6710826(R)-2-Thiophen-2-ylthiazolidine-4-carboxylic acidHCID 23681850Potassium thiobenzoate

生成物 1

HCID 12915812(4R)-3-(S-Benzoyl-3-mercaptopropanoyl)-2-(2-thienyl)-4-thiazolidinecarboxylic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

10.8 g of (4R)-2-(2-thienyl)-4-thiazolidinecarboxylic acid and 10.6 g of sodium carbonate are dissolved in 100 ml of water and 8.6 g of 3-bromopropanoyl chloride is added dropwise while stirring under ice-cooling. After the addition, the mixture is stirred under ice-cooling for 2 hours. To this reaction solution, 8.8 g of potassium thiobenzoate is added and stirred at room temperature for 1 hour. The solution is acidified with dilute hydrochloric acid and the produced oil is extracted with ethyl acetate. The ethyl acetate layer is washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the titled compound, yield 11.6 g (57%), mp. 141°-143° C. (benzene), [α]D25 +107.7° (c=1.0, methanol).

後処理

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture is stirred under ice-
  4. temperaturecooling for 2 hours
  5. stirringstirred at room temperature for 1 hour
  6. extractionthe produced oil is extracted with ethyl acetate
  7. washThe ethyl acetate layer is washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6e543fa49c8c42239432736afe6bae55
出典データセット
uspto-grants-1984_02
特許番号
US04430344

反応ノート

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