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

HRID 1349370
ノート
印刷プレビュー

反応式

HRID 1349370 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2cbbebd2a3b94d5bbd2dbd37068a7e93
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07211680B2

反応ノート

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