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

HRID 1173773
Notes
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Reaction equation

HRID 1173773 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Conditions

Temperature
5 °C

Procedure

(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%).

Workup

  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

Sources & evidence

ORD record
ord-8c40bcfd443442959a73bb2cfbb74730
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07834190B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes