4-Toluenesulfonyl chloride → Nalpha, Nepsilon-di-(4-methylbenzenesulfonyl)-L-lysine

HRID 1282503

反応式

HRID 1282503 の反応式
Cl.Cl.[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1.C([O-])([O-])=O.[K+].[K+]>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)(=[O:22])=[O:21])(=[O:22])=[O:21])=[CH:16][CH:15]=1

参加物

5

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 69567Lysine dihydrochloride

生成物 1

HCID 15696926Nalpha, Nepsilon-di-(4-methylbenzenesulfonyl)-L-lysine収率 75%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 11430Potassium Carbonate溶媒

実験手順

To a stirred solution of L-lysine dihydrochloride (1 mmol) in a mixture of THF and 1M K2CO3 (3 mL/3 mL) was added 4-methylbenzenesulfonyl chloride (381 mg, 2.00 mmol). The reaction mixture was stirred for 2 h and then quenched with 1N HCl and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated. The crude was purified by flash chromatography using hexane/EtOAc/AcOH (30:69.4/0.6) to give 75% of the desired product.

後処理

  1. customquenched with 1N HCl
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified by flash chromatography

出典と根拠

ORDレコード
ord-915d743dfdb241378e7ba9e2653a7af0
出典データセット
uspto-grants-2002_09
特許番号
US06455587B1

関連ノート

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