Dimethylamine → Benzyl N-[3-(dimethylcarbamoyl)propyl]carbamate

HRID 17424

반응식

HRID 17424 반응식
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:19]([N:21]=[C:22]=NCCCN(C)C)C.CN(CCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1.CNC>CN(C)C=O>[CH3:19][N:21]([CH3:22])[C:15]([CH2:14][CH2:13][CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:17]

참가 물질

6

반응물 4

HCID 674DimethylamineHCID 211844-(((Benzyloxy)carbonyl)amino)butanoic acidHCID 757711-HydroxybenzotriazoleHCID 866308461-(Dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

생성물 1

HCID 16754355Benzyl N-[3-(dimethylcarbamoyl)propyl]carbamate수율 82.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(Benzyloxycarbonylamino)butyric acid (0.74 g, 3.12 mmol) was dissolved in N,N-dimethylformamide, then 1-(dimethylaminopropyl)-3-ethylcarbodiimide 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.60 g, 3.13 mmol), 1-hydroxybenzotriazole (0.48 g, 3.13 mmol) and dimethylamine (2.0 M tetrahydrofuran solution, 2.40 ml, 4.80 mmol) were added, followed by stirring at room temperature for 3 days. The reaction liquid was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=70:1 to 40:1) to obtain a yellow solid (0.68 g, 82%).

후처리

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated away under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (dichloromethane:methanol=70:1 to 40:1)

출처 및 근거

ORD 기록
ord-3c82f86e57194445b5a85b886244c1a5
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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