Dicyclohexylcarbodiimide → Succinic 2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester 2,5-dioxo-pyrollidine-1-yl ester
Reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH2:9]([O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:25](=[O:31])[CH2:26][CH2:27][C:28](O)=[O:29])[CH:10]=[CH2:11].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:28](=[O:29])[CH2:27][CH2:26][C:25]([O:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:9][CH:10]=[CH2:11])=[O:31]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
N-hydroxysuccin imide (1.58 g, 13.8 mmol) and succinic mono-(2-{2-[2-(2-allyloxy-ethoxy)-ethoxy]-ethoxy}-ethyl) ester (10) (4.6 g, 13.76 mmol) were dissolved in dry CH2Cl2 (10 mL) at room temperature. A solution of N,N′-dicyclohexylcarbodiimide (DCC) (2.84 g, 13.8 mmol) in dry CH2Cl2 (2 mL) was slowly added to the mixture at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The solid residues in the reaction mixture were filtered through a sintered glass filter and removed and the filtrate was concentrated to obtain the target compound in a yellow oily phase (5.5 g, 93%). The compound was used without further purification. The NMR analysis result of the product is as follows.
Workup
- filtrationThe solid residues in the reaction mixture were filtered through a sintered glass
- filtrationfilter
- customremoved
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-86e1bc0317704481a68262c2fb33822c
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718577B2
Reaction notes
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