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Dimethylformamide → Ethyl 4-[2-[3-[2-(tert-butoxycarbonylamino)ethyl]phenoxy]-3-pyridyl]aminobutyrate

HRID 1373230
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HRID 1373230 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[O:16][C:17]1[C:22]([NH:23][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:24])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 21073097Tert-butyl[2-[3-(3-amino-2-pyridyloxy)phenyl]ethyl]carbamate

생성물 1

HCID 21072933Ethyl 4-[2-[3-[2-(tert-butoxycarbonylamino)ethyl]phenoxy]-3-pyridyl]aminobutyrate수율 54.4%

시약·촉매·용매 1

HCID 962
Water
용매

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온도
60 °C

실험 절차

A mixture of tert-butyl[2-[3-(3-amino-2-pyridyloxy)phenyl]ethyl]carbamate (3.3 g, 10 mmols), ethyl 4-bromobutyrate (2.8 ml, 20 mmols), potassium carbonate (1.4 g, 10 mmols) and N,N-dimethylformamide (30 ml) was stirred at 60° C. for 72 hours. The reaction mixture was cooled, then poured into water, and extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography to give an oil of ethyl 4-[2-[3-[2-(tert-butoxycarbonylamino)ethyl]phenoxy]-3-pyridyl]aminobutyrate (2.41 g, 54.4%).

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography

출처 및 근거

ORD 기록
ord-000a912da71d47adbd0f663f05c95c7e
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07160887B1

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