DL-Homoserine → (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide

HRID 266354

反応式

HRID 266354 の反応式
[NH2:1][CH:2]([CH2:6][CH2:7][OH:8])[C:3]([OH:5])=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O.C1COCC1>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28]([NH:1][CH:2]2[CH2:6][CH2:7][O:8][C:3]2=[O:5])(=[O:30])=[O:29])=[CH:24][CH:23]=1

参加物

7

反応物 4

HCID 779DL-HomoserineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

生成物 1

HCID 19032731(RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide収率 60.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

(RS)-2-amino-4-hydroxybutanoic acid (2.0438 g) was dissolved in water (20 ml). The solution was cooled to 0° C., and potassium carbonate (5.217 g) and ethyl acetate (20 ml) were added. Then, p-chlorobenzenesulfonyl chloride (9.0536 g) and THF (2 ml) were added, and the whole was stirred overnight. After the reaction was completed, the ethyl acetate layer was separated. The aqueous layer was acidified with 2N HCl and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated to give a crude product. The crude product was purified by silica gel column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-4-butanolide (2.8674 g).

後処理

  1. customthe ethyl acetate layer was separated
  2. extractionextracted with ethyl acetate
  3. concentrationThe combined ethyl acetate layers were concentrated
  4. customto give a crude product
  5. customThe crude product was purified by silica gel column chromatography (silica gel 50 g, hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-b9c6c5a45e164ac8aa66d3c6f2f83ebc
出典データセット
uspto-grants-1997_07
特許番号
US05650428

関連ノート

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