Water → N-Methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-(thiophen-2-yl)ethyl) carbamoyl)-2-(2-naphthyl)ethyl) carbamic acid tert butylester

HRID 1268637노트

반응식

HRID 1268637 반응식
C(OC([CH2:8][NH:9][CH:10]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)[C:11]([OH:13])=O)=O)(C)(C)C.ON1C2N=C[CH:33]=[CH:34][C:29]=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH3:47][NH:48][C:49](=[O:59])[C@H:50]([NH:57][CH3:58])[CH2:51][C:52]1[S:53][CH:54]=[CH:55][CH:56]=1.CN[C:62](=[O:72])C(NC)CC1SC=CC=1.[CH:73](NC(C)C)(C)C.[OH2:80]>C(Cl)Cl>[C:34]([O:80][C:62](=[O:72])[N:9]([CH3:8])[C@@H:10]([C:11](=[O:13])[N:57]([CH3:58])[C@@H:50]([C:49](=[O:59])[NH:48][CH3:47])[CH2:51][C:52]1[S:53][CH:54]=[CH:55][CH:56]=1)[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1)([CH3:33])([CH3:29])[CH3:73]

참가 물질

9

반응물 7

HCID 962WaterHCID 7912DiisopropylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10535973(2R)-N-methyl-2-methylamino-3-(thiophen-2-yl)propionamideHCID 223270012-(Tert-butoxycarbonylmethylamino)-3-(2-naphthyl)propionic acidHCID 22327074N-Methyl-2-methylamino-3-(thiophen-2-yl)propionamide

생성물 1

HCID 10767985N-Methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-(thiophen-2-yl)ethyl) carbamoyl)-2-(2-naphthyl)ethyl) carbamic acid tert butylester

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

2-(tert Butoxycarbonylmethylamino)-3-(2-naphthyl)propionic acid (1.20 g; 3.55 mmol) was dissolved in methylene chloride (10 ml). 1-Hydroxy-7-azabenzotriazol (0.48 g ;3.55 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.75 g; 3.90 mmol) were added. The reaction mixture was stirred for 15 min at room temperature. 2R)-N-Methyl-2-methylamino-3-(thiophen-2-yl)propionamide (0.70 g; 3.55 mmol) was dissolved in methylene chloride (10 ml) and added. Diisopropylamine (0.61 ml; 3.55 mmol) was added. The reaction mixture was stirred at room temperature for 2 days. Methylene chloride (10 ml) and water (10 ml) were added to the reaction mixture. The phases were separated and the organic phase was washed with aqueous sodium hydrogensulfate (10%; 20 ml), saturated aqueous sodium hydrogencarbonate (20 ml). The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo. The crude product was chromatographed on silica (2×20 cm) using ethylacetate/heptane (1:1) as eluent to afford 1.38 g of N-methyl-N-((1R)-1-(N-methyl-N-((1R)-1-(methylcarbamoyl)-2-(thiophen-2-yl)ethyl)carbamoyl)-2-(2-naphthyl)ethyl) carbamic acid tert butylester.

후처리

  1. additionadded
  2. stirringThe reaction mixture was stirred at room temperature for 2 days
  3. customThe phases were separated
  4. washthe organic phase was washed with aqueous sodium hydrogensulfate (10%; 20 ml), saturated aqueous sodium hydrogencarbonate (20 ml)
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customThe crude product was chromatographed on silica (2×20 cm)

출처 및 근거

ORD 기록
ord-8fe0851534f64c53be883483b7407daf
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06555570B2

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