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Dimethylformamide → N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamide

HRID 1039288
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HRID 1039288 반응식
[CH2:1]([O:8][CH:9]([CH3:15])[CH2:10][CH2:11][C:12]([OH:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.Cl.[NH2:28][C:29]1[C:37]([OH:38])=[C:36]2[C:32]([CH2:33][CH2:34][CH:35]2[CH2:39][CH2:40][NH:41][C:42](=[O:44])[CH3:43])=[CH:31][CH:30]=1>O1CCCC1.N1C=CC=CC=1>[C:42]([NH:41][CH2:40][CH2:39][CH:35]1[C:36]2[C:32](=[CH:31][CH:30]=[C:29]([NH:28][C:12](=[O:14])[CH2:11][CH2:10][CH:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH3:15])[C:37]=2[OH:38])[CH2:33][CH2:34]1)(=[O:44])[CH3:43]
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 577812604-(Benzyloxy)pentanoic AcidHCID 67354374N-[2-(6-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide Hydrochloride

생성물 1

HCID 57781273N-{3-[2-(Acetylamino)ethyl]-4-hydroxy-2,3-dihydro-1H-inden-5-yl}-4-(benzyloxy)pentanamide수율 57.4%

시약·촉매·용매 2

HCID 1049Pyridine용매
HCID 8028Tetrahydrofuran용매

실험 절차

4-(Benzyloxy)pentanoic acid (230 mg, 1.10 mmol) was dissolved in tetrahydrofuran (10 mL), oxalyl chloride (90 μL, 1.05 mmol) and dimethylformamide (10 μL) were added under ice-cooling, and the mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, and the residue was diluted with dichloromethane (1 mL). This was added to a solution of N-[2-(6-amino-7-hydroxy-2,3-dihydro-1H-inden-1-yl)ethyl]acetamide hydrochloride (244 mg, 0.903 mmol) in pyridine (10 mL) under ice-cooling, and the mixture was stirred at room temperature for 15 min. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0) to give the title compound (220 mg, yield 57%).

후처리

  1. temperaturecooling
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with dichloromethane (1 mL)
  4. temperaturecooling
  5. stirringthe mixture was stirred at room temperature for 15 min
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=80/20→100/0)

출처 및 근거

ORD 기록
ord-146d6933e0bb42c1b5744f47a8ab6869
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552037B2

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