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

HRID 1173773
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HRID 1173773 반응식
[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
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 7964Chlorobenzene용매

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온도
5 °C

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-8c40bcfd443442959a73bb2cfbb74730
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834190B2

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