Diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate → (4S,5R)-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

HRID 2413383Notes

Reaction equation

HRID 2413383 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@H:11]([C:18]([O:20]CC)=[O:19])[N:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>P([O-])([O-])([O-])=O>[CH2:1]([N:8]1[C@@H:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C@@H:11]([C:18]([OH:20])=[O:19])[N:10]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 13276246Diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Product 1

HCID 13255427(4S,5R)-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A suspension of diethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (500 mg) in 0.1m phosphate buffer (pH 8.0, 50 ml) was treated with Pig Liver Esterase (manufactured by Sigma Lab., 1600 units, 10 mg) in a manner similar to that in Example 1 (1) to give (4S,5R)-1,3-dibenzyl-5-ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (400 mg). M.P., 108°-112° C. [α]D20 =+4.4° (c=1, CHCl3).

Sources & evidence

ORD record
ord-586f81cdff994013923c7c5fec36e001
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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