1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 950483-64-4
Reaction equation
[CH2:1]([C@H:4]1[O:6][C@@H:5]1[C:7]([OH:9])=O)[CH2:2][CH3:3].[CH:10]1([NH2:13])[CH2:12][CH2:11]1.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH:10]1([NH:13][C:7]([C@@H:5]2[C@@H:4]([CH2:1][CH2:2][CH3:3])[O:6]2)=[O:9])[CH2:12][CH2:11]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
(2S,3R)-3-Propyl-2-oxiranecarboxylic acid (1.16 g, 7.8 mmol), methylene chloride (10 ml) and cyclopropylamine (8.5 equivalents) were mixed, and the mixture was cooled to 5° C. A methylene chloride solution (5 ml) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.23 g, 1.2 equivalents) was gradually added thereto, and the mixture was stirred for 2 hours from 5° C. up to room temperature. The organic layer was washed with water (5 ml), 1 N HCl (5 ml) and water (5 ml); and was dried with anhydrous magnesium sulfate. The inorganic products were separated by filtration, and the filtrate was concentrated under reduced pressure to obtain the title compound as a pale yellow solid (0.70 g, yield: 53%).
Workup
- washThe organic layer was washed with water (5 ml), 1 N HCl (5 ml) and water (5 ml)
- dry with materialand was dried with anhydrous magnesium sulfate
- customThe inorganic products were separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2224a5bf87ed45ca9595a0b3601e5bce
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07834190B2
Reaction notes
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