1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl {2-[({5-[(tert-butoxycarbonyl)amino]-3-methylthiophen-2-yl}carbonyl)(methyl)amino]ethyl}methylcarbamate

HRID 446584노트

반응식

HRID 446584 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([OH:16])=O)=[C:11]([CH3:17])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH2:27][CH2:28][NH:29][CH3:30])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]([N:29]([CH3:30])[CH2:28][CH2:27][N:19]([CH3:18])[C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:16])=[C:11]([CH3:17])[CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 434168385-((tert-Butoxycarbonyl)amino)-3-methylthiophene-2-carboxylic acid

생성물 1

HCID 86663470tert-Butyl {2-[({5-[(tert-butoxycarbonyl)amino]-3-methylthiophen-2-yl}carbonyl)(methyl)amino]ethyl}methylcarbamate수율 79%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

The compound (600 mg, 2.33 mmol) obtained in Example 89a and tert-butyl methyl[2-(methylamino)ethyl]carbamate (439 mg, 2.33 mmol) described in the literature (J. Med. Chem. 1990, 33, 97) were dissolved in methylene chloride (23 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (670 mg, 3.50 mmol) and 4-dimethylaminopyridine (14 mg, 0.117 mmol) were added, and the mixture was stirred at room temperature for 1.5 hours. The solvent was evaporated under reduced pressure, 1 N hydrochloric acid was added to the resulting residue, the mixture was extracted with ethyl acetate, and then the organic layer was washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1, v/v) to give the title compound (757 mg; yield, 79%) as a light yellow solid.

후처리

  1. customThe solvent was evaporated under reduced pressure, 1 N hydrochloric acid
  2. additionwas added to the resulting residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated sodium chloride solution
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (hexane

출처 및 근거

ORD 기록
ord-fb9c7a073fac4ace99bd3b15a581d7aa
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476253B2

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