4-Methylmorpholine → N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide

HRID 2209683

반응식

HRID 2209683 반응식
[Li+].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:14]([CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:15]([O-])=[O:16])(=[O:12])=[O:11])=[CH:6][CH:5]=1.CN1CCOCC1.O.ON1C2C=CC=CC=2N=N1.Cl.[C:51]([O:55][NH2:56])([CH3:54])([CH3:53])[CH3:52].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl>[C:51]([O:55][NH:56][C:15](=[O:16])[C@H:14]([N:13]([S:10]([C:7]1[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11])[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])([CH3:54])([CH3:53])[CH3:52]

참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 700596162(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanoic acid lithium salt

생성물 1

HCID 10625382N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanoic acid lithium salt (4.42 g, 10.18 mmol) in methylene chloride (100 mL) containing N-methylmorpholine (6.73 mL, 61.06 mmol), 1-hydroxybenzotriazole monohydrate (1.64 g, 10.687 mmol) and O-t-butylhydroxyl amine hydrochloride (1.41 g, 11.20 mmol) is added N-[dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.90 g, 20.36 mmol) at 0° C. The reaction mixture is allowed to warm to room temperature and stirring is continued overnight. The mixture is diluted with methylene chloride, washed with saturated sodium bicarbonate, then with brine, dried (Na2SO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (10:1:0.5 ethyl acetate/methanol/ammonium hydroxide) to provide N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](benzyl)amino]-6-(N,N-dimethylamino) hexanamide.

후처리

  1. washwashed with saturated sodium bicarbonate
  2. dry with materialwith brine, dried (Na2SO4)
  3. customthe solvent is evaporated
  4. customThe crude product is purified by silica gel chromatography (10:1:0.5 ethyl acetate/methanol/ammonium hydroxide)

출처 및 근거

ORD 기록
ord-cd2668f60d724b73a9dc7b4d51760cc7
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05455258

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