Di-n-propyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate → (4S,5R)-1,3-dibenzyl-5-n-propoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

HRID 2413385Notes

Reaction equation

HRID 2413385 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([O:15][CH2:16][CH2:17][CH3:18])=[O:14])[C@H:11]([C:19]([O:21]CCC)=[O:20])[N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:32])[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][CH2:17][CH3:18])=[O:14])[C@@H:11]([C:19]([OH:21])=[O:20])[N:10]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 18595938Di-n-propyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Product 1

HCID 13276243(4S,5R)-1,3-dibenzyl-5-n-propoxycarbonyl-2-oxoimidazolidine-4-carboxylic acidYield 90.7%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A suspension of di-n-propyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (200 mg) in 0.1m phosphate buffer (pH 8.0, 20 ml) was treated with Pig Liver Esterase (manufactured by Sigma Lab., 640 units, 4 mg) in a manner similar to that in Example 1 (1) to give (4S,5R)-1,3-dibenzyl-5-n-propoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (164 mg). M.P., 75°-90° C. [α]D20 =+2.1° (c=1, CHCl3).

Sources & evidence

ORD record
ord-cac71ca64afd4fdc94e11e32f87c2592
Source dataset
uspto-grants-1985_01
Patent number
US04496739

Reaction notes

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