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Cyclopropylamine → (2S,3R)-3-benzyl-2-oxiranecarboxylic cyclopropylamide

HRID 1173773
ノート
印刷プレビュー

反応式

HRID 1173773 の反応式
[CH2:1]([C@H:8]1[O:10][C@@H:9]1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14]1([NH2:17])[CH2:16][CH2:15]1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)Cl.ClC1C=CC=CC=1>[CH:14]1([NH:17][C:11]([C@@H:9]2[C@@H:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:10]2)=[O:13])[CH2:16][CH2:15]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22867771(2S,3R)-3-benzyl-2-oxiranecarboxylic acid

生成物 1

HCID 59203389(2S,3R)-3-benzyl-2-oxiranecarboxylic cyclopropylamide収率 62.1%

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 7964Chlorobenzene溶媒

反応条件

温度
5 °C

実験手順

(2S,3R)-3-Benzyl-2-oxiranecarboxylic acid (66 mg) and a chlorobenzene solution (2 ml) of cyclopropylamine (23.2 mg, 1.1 equivalents) were mixed, and the mixture was cooled to 5° C. A methylene chloride solution (2 ml) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.5 equivalents) was gradually added, and the mixture was stirred at room temperature for 14 hours. Saturated aqueous solution of sodium hydrogencarbonate (5 ml) was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate (10 ml). The organic layer was washed with 1 N hydrochloric acid (5 ml) and water (5 ml) in order, and the solvent was evaporated away under reduced pressure to obtain the title compound as a brown oil (50 mg, yield: 62%).

後処理

  1. extractionthe reaction mixture was extracted with ethyl acetate (10 ml)
  2. washThe organic layer was washed with 1 N hydrochloric acid (5 ml) and water (5 ml) in order
  3. customthe solvent was evaporated away under reduced pressure

出典と根拠

ORDレコード
ord-8c40bcfd443442959a73bb2cfbb74730
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07834190B2

反応ノート

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