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

HRID 463725Notes

Reaction equation

HRID 463725 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.C(Cl)(Cl)Cl.S(=O)(=O)(O)O>P([O-])([O-])([O-])=O>[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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6212ChloroformHCID 11234411Dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate

Product 1

HCID 11152843(4S,5R)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

To a suspension of dimethyl cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylate (500 mg) in 0.1M phosphate buffer (pH 8.0, 50 ml) was added Pig Liver Esterase (manufactured by Sigma Lab., 1600 units, 10 mg). The mixture was stirred at room temperature for 30 hours. Chloroform (150 ml) was added to the mixture. Then, the mixture was adjusted to pH 2 with diluted sulfuric acid. The chloroform layer was separated from the aqueous layer, washed with water, dried over anhydrous magnesium sulfate and concentrated to give (4S,5R)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (435 mg). M.P., 141°-146° C. [α]D20 =+2.0° (c=1, CHCl3). [α]36520 =-21.6° (c=1, DMF).

Workup

  1. additionwas added Pig Liver Esterase (manufactured by Sigma Lab., 1600 units, 10 mg)
  2. customThe chloroform layer was separated from the aqueous layer
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-798d86f268d3419bb625b367526ca523
Source dataset
uspto-grants-1985_10
Patent number
US04544635

Reaction notes

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