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

HRID 463731Notes

Reaction equation

HRID 463731 reaction equation
[CH2:1]([N:8]1[C@H:12]([C:13]([O:15][CH2:16][CH2:17][CH2:18][CH3:19])=[O:14])[C@H:11]([C:20]([O:22]CCCC)=[O:21])[N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:34])[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][CH2:18][CH3:19])=[O:14])[C@@H:11]([C:20]([OH:22])=[O:21])[N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:9]1=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 18595937Di-n-butyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Product 1

HCID 13279710(4S,5R)-1,3-dibenzyl-5-n-butyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A suspension of di-n-butyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (500 mg) in 0.1M phosphate buffer (pH 8.0, 45 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-n-butyloxycarbonyl-2-oxoimidazolidine-4-carboxylic acid as an oily product. [α]D20 =+4.1° (c=1.55, CHCl3).

Sources & evidence

ORD record
ord-9e4ad9a67c864589accadf45993d41ca
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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