Cyclopropylamine → (2S,3R)-3-benzyl-2-oxiranecarboxylic cyclopropylamide
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]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
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
- extractionthe reaction mixture was extracted with ethyl acetate (10 ml)
- washThe organic layer was washed with 1 N hydrochloric acid (5 ml) and water (5 ml) in order
- customthe solvent was evaporated away under reduced pressure
Sources & evidence
- ORD record
- ord-8c40bcfd443442959a73bb2cfbb74730
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834190B2
Reaction notes
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