L-Threonine → HCID 178462331、化合物

HRID 484674

反応式

HRID 484674 の反応式
[NH2:1][C@H:2]([C:6]([OH:8])=O)[C@@H:3]([CH3:5])[OH:4].[OH-].[Na+].[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1SCl)([O-:13])=[O:12].[S:22](=O)(=O)(O)[O-].[K+]>O.O1CCOCC1>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:1][C@H:2]([C:6]([OH:8])=[S:22])[C@@H:3]([CH3:5])[OH:4])([O-:13])=[O:12]

参加物

7

反応物 4

HCID 6288L-ThreonineHCID 14798Sodium Hydroxide2 回HCID 243192-Nitrobenzenesulfenyl chlorideHCID 516920Potassium bisulfate

生成物 1

HCID 178462331HCID 178462331、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

L-threonine (11.9 g) is added to dioxane (125 ml) and 2N sodium hydroxide (50 ml). To the vigorously stirred solution, o-nitrophenylsulfenyl chloride (20.9 g) is added in ten equal portions over fifteen minutes, while 2N sodium hydroxide (60 ml) is slowly added dropwise. After five more minutes the reaction mixture is diluted with water (400 ml) and acidified to pH 2.5 with 10% potassium bisulfate. The organic layer is immediately extracted with ethyl acetate (three 200 ml portions), and the combined extracts are dried over sodium sulfate, and then concentrated to an oil. The product crystallizes on scratching (20.0 g). Recrystallization of 17 g from acetone/hexane affords 9.5 g of crystals, melting point 145°-148° C. which are stored in a freezer and used promptly.

後処理

  1. additionis slowly added dropwise
  2. extractionThe organic layer is immediately extracted with ethyl acetate (three 200 ml portions)
  3. dry with materialthe combined extracts are dried over sodium sulfate
  4. concentrationconcentrated to an oil
  5. customThe product crystallizes
  6. customRecrystallization of 17 g from acetone/hexane

出典と根拠

ORDレコード
ord-e98c98c1543c45a58e965f9f8433e5b6
出典データセット
uspto-grants-1985_08
特許番号
US04533660

関連ノート

読み込み中…