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

HRID 1282503

반응식

HRID 1282503 반응식
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

참가 물질

5

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 69567Lysine dihydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 11430Potassium Carbonate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-915d743dfdb241378e7ba9e2653a7af0
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455587B1

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