Sodium hydride → 3-(2,2'-Bisethylcarbamoyl-2-phenylethoxy)propionic acid methyl ester
Reaction equation
[H-].[Na+].[CH2:3]([NH:5][C:6](=[O:21])[C:7]([CH2:19][OH:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]([NH:10][CH2:11][CH3:12])=[O:9])[CH3:4].Br[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][O:20][CH2:19][C:7]([C:6](=[O:21])[NH:5][CH2:3][CH3:4])([C:8](=[O:9])[NH:10][CH2:11][CH3:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Sodium hydride (89 mg) was dissolved in THF (5 ml), and the solution was cooled to 0° C. and thereto were added a THF solution (1 ml) of N,N′-diethyl-2-hydroxymethyl-2-phenylmalonamide (400 mg) and tetrabutyl ammonium iodide (10 mg). After addition of a THF solution (2 mL) of methyl 3-bromopropionate (314 mg), the resulting mixture was stirred overnight at room temperature, and further at 60° C. for 0.5 hour. The reaction solution was filtered through a Celite, and the filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to give 3-(2,2′-bisethylcarbamoyl-2-phenylethoxy)propionic acid methyl ester (175 mg).
Workup
- waitfurther at 60° C. for 0.5 hour
- filtrationThe reaction solution was filtered through a Celite
- concentrationthe filtrate was concentrated
- custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:1)
Sources & evidence
- ORD record
- ord-b52824a1f60d49108eb50a971f1ef1a2
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07432392B2
Reaction notes
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