Potassium Carbonate → 1-[2-benzoylthio-3-methoxybutanoyl]L-proline

HRID 262724ノート

反応式

HRID 262724 の反応式
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Br[CH:10]([CH:14]([O:16][CH3:17])[CH3:15])[C:11](Cl)=[O:12].[C:18]([OH:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[OH-].[Na+]>[C:18]([S:25][CH:10]([CH:14]([O:16][CH3:17])[CH3:15])[C:11]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:12])(=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 130170472-Bromo-3-methoxybutyryl chlorideHCID 178526132HCID 178526132、化合物

生成物 1

HCID 186324661-[2-benzoylthio-3-methoxybutanoyl]L-proline

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

実験手順

To a solution of L-proline (5.75 g.) in N sodium hydroxide (50 ml.) chilled in an ice bath, 2 N sodium hydroxide (25 ml.) and 2-bromo-3-methoxybutyric acid chloride [obtained from 2-bromo-3-methoxybutyric acid [J. Am. Chem. Soc., 71, 1096, (1949)] and thionyl chloride] (10.7 g.) are added, with vigorous stirring. After three hours, thiobenzoic acid (7.5 g.) and potassium carbonate (4.8 g.) are added and the mixture is stirred at room temperature overnight. The reaction mixture is acidified and extracted with ethyl acetate. The organic layer is concentrated to dryness and the residue is chromatographed on a column of silica gel with benzene-acetic acid to yield 1-[2-benzoylthio-3-methoxybutanoyl]-L-proline.

後処理

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer is concentrated to dryness
  3. customthe residue is chromatographed on a column of silica gel with benzene-acetic acid

出典と根拠

ORDレコード
ord-0e2df6cf48ae4373b31c2a5f1e4d3d54
出典データセット
uspto-grants-1979_05
特許番号
US04154936

反応ノート

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