4-Methylmorpholine → N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide

HRID 264281

반응식

HRID 264281 반응식
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]([CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[C@H:14]([CH:18]([CH3:20])[CH3:19])[C:15]([OH:17])=O)(=[O:12])=[O:11])=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.Cl.[C:46]([O:50][NH2:51])([CH3:49])([CH3:48])[CH3:47].Cl.CN(CCCN=C=NCC)C>C(Cl)Cl.O>[C:46]([O:50][NH:51][C:15](=[O:17])[C@H:14]([N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=1)(=[O:11])=[O:12])[CH2:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)[CH:18]([CH3:19])[CH3:20])([CH3:49])([CH3:48])[CH3:47]

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 700617032(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methyl-butanoic acid hydrochloride

생성물 1

HCID 10671218N-(t-Butyloxy)-2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

2(R)-[[4-methoxybenzenesulfonyl](3-picolyl)amino]-3-methylbutanoic acid hydrochloride (5.0 g, 12.06 mmol), 1-hydroxybenzotriazole (1.63 g, 12.06 mmol), 4-methylmorpholine (6.6 mL, 60.31 mmol), and O-t-butylhydroxylamine hydrochloride (54.55 g, 36.19 mmol) are dissolved in methylene chloride (200 mL). N-[Dimethylaminopropyl]-N'-ethylcarbodiimide hydrochloride (3.01 g, 15.68 mmol) is added, and the reaction is stirred overnight. The reaction is then diluted with water and extracted with methylene chloride. The combined organic extracts are washed with brine, dried (Na2SO4), and the solvent is evaporated. The crude product is purified by silica gel chromatography (2% methanol/methylene chloride) to give N-(t-butyloxy)-2(R)-[[4-methoxybenzenesulfonyl]-(3-picolyl)amino]-3-methylbutanamide.

후처리

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (Na2SO4)
  4. customthe solvent is evaporated
  5. customThe crude product is purified by silica gel chromatography (2% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-41514be63049496481ae56f3c5220799
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646167

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