Sulfuric Acid → (4S,5R)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

HRID 463726Notes

Reaction equation

[CH2:1]([N:8]1[C@H:12]([C:13]([O:15][CH3:16])=[O:14])[C@H:11]([C:17]([O:19]C)=[O:18])[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(Cl)(Cl)Cl.S(=O)(=O)(O)O>P([O-])([O-])([O-])=O.CO>[CH2:1]([N:8]1[C@@H:12]([C:13]([O:15][CH3:16])=[O:14])[C@@H:11]([C:17]([OH:19])=[O:18])[N:10]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (10.0 g) in a mixture of 0.1M phosphate buffer (pH 8.0, 900 ml) and methanol (100 ml) was added Pig Liver Esterase (manufactured by Sigma Lab., 32000 units, 200 mg). The mixture was stirred at 30° C. for 42 hours while the pH was adjusted to around 8.0 with 1N aqueous sodium hydroxide solution. Chloroform (500 ml) was added to the mixture. Then, the mixture was adjusted to pH 2 with diluted sulfuric acid. The aqueous and chloroform layers were separated. The chloroform layer was washed with water, dried over anhydrous magnesium sulfate and concentrated to give (4S,5R)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (8.80 g). M.P., 145°-147° C. [α]36520 =-25.3° (c=1, DMF).

Workup

additionwas added Pig Liver Esterase (manufactured by Sigma Lab., 32000 units, 200 mg)
customThe aqueous and chloroform layers were separated
washThe chloroform layer was washed with water
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-6c24856960424dfc99bdb9eb6b51cdba
Source dataset: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04544635

Reaction notes

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