Carbamate → Mandelic Acid

HRID 1154497Notes

Reaction equation

HRID 1154497 reaction equation
C1(C2[O:11][C:10](=[O:12])[NH:9]C2=O)C=CC=CC=1.C(=O)([O-])N.[C:18]([OH:28])(=[O:27])[C@@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:20]>>[C:18]([OH:28])(=[O:27])[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:20].[C:10](=[O:11])([OH:12])[NH2:9].[C:18]([OH:28])(=[O:27])[C@@H:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:20]

Participants

5

Reactant 3

HCID 276CarbamateHCID 11914(-)-Mandelic acidHCID 840425-Phenyloxazolidine-2,4-dione

Product 2

HCID 1292Mandelic AcidHCID 131714067HCID 131714067, compound

Procedure

According to the present invention, the carbamyl derivative of D(-) madelic acid can be advantageously prepared by the stereoselective enzymatic hydrolysis of the corresponding 5-phenyl-2,4-oxazolidinedione. A further considerable advantage of the process according to the present invention is that the enzymatic reaction substrate recemises spontaneously under the hydrolysis conditions, so that at the end of the reaction the carbamate of the D-mandelic acid is obtained in a stoichiometric quantity with respect to the starting substrate. The reaction scheme is as follows: ##STR5## D(-) mandelic acid is then obtained from the D-mandelic acid carbamate by hydrolysis in an acid environment.

Workup

  1. customis obtained in a stoichiometric quantity with respect to the starting substrate
  2. customThe reaction scheme

Sources & evidence

ORD record
ord-04c03280c2c1441f9dcff702aa3fced0
Source dataset
uspto-grants-1984_12
Patent number
US04489208

Reaction notes

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