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Dicyclohexylcarbodiimide → 1-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide

HRID 1359556
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HRID 1359556 반응식
C1(N=C=NC2CCCCC2)CCCCC1.[Br:16][C:17]1([C:20]([OH:22])=O)[CH2:19][CH2:18]1.O[N:24]1[C:28](=[O:29])[CH2:27][CH2:26][C:25]1=O.NC(CC)CO>C(Cl)Cl>[Br:16][C:17]1([C:20]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])=[O:22])[CH2:19][CH2:18]1
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참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 221292-Amino-1-butanolHCID 80170N-HydroxysuccinimideHCID 128674801-Bromocyclopropane-1-carboxylic acid

생성물 1

HCID 694261281-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide수율 76%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

7.45 g of N,N′-dicyclohexylcarbodiimide is added at 0° C. under nitrogen to a solution of 5.0 g of 1-bromocyclopropanecarboxylic acid 4 and 4.18 g of N-hydroxysuccinimide in 87 ml of methylene chloride, and it is stirred for 1.5 more hours. Then, 7.46 ml of 2-amino-1-butanol is added, and it is stirred for 2 hours at room temperature. After dilution with methylene chloride, it is filtered, concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate/hexane. 5.44 g of 1-bromo-N-[(1-hydroxymethyl)propyl]-cyclopropane-1-carboxamide 78 is obtained as a yellowish oil.

후처리

  1. stirringit is stirred for 2 hours at room temperature
  2. filtrationAfter dilution with methylene chloride, it is filtered
  3. concentrationconcentrated by evaporation
  4. customthe residue is chromatographed on silica gel with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-fbbe495f68b54d2581ba5c5f4da333cd
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06600058B1

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