Atrolactic acid → (S)-Atrolactic acid

HRID 1399485

Reaction equation

HRID 1399485 reaction equation
[C:1]1([C:7]([CH3:12])([OH:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(NCC(O)=O)C=CC=CC=1.ClC1C=CC=CC=1C(O)C(O)=O>>[C:1]1([C@:7]([CH3:12])([OH:11])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 1303Atrolactic acidHCID 66025N-PhenylglycineHCID 977202-Chloromandelic acid

Product 1

HCID 445144(S)-Atrolactic acid

Procedure

The analysis of phenyllactic acid was initially plagued with the same problems discussed for phenylglycine and 2-chloromandelic acid. However, in this case, adjustment of the solvent concentration in the nonchiral HPLC method led to a shift in the retention time of the acid, so that it no longer coeluted with the cell lysate peak. Following this, no problems were encountered with either the nonchiral or chiral methods. Representative nonchiral chromatograms of the product (1.9 min) and cyanohydrin substrate (3.7 min) are shown in FIG. 8A, while the chiral analysis of the acid is shown in FIG. 8B, with the L-enantiomer eluting at 2 min and the opposite enantiomer at 6 min.

Workup

  1. concentrationHowever, in this case, adjustment of the solvent concentration in the nonchiral HPLC method
  2. customRepresentative nonchiral chromatograms of the product (1.9 min) and cyanohydrin substrate (3.7 min)
  3. customat 6 min.

Sources & evidence

ORD record
ord-1c24f8bcb4bd47e8a9373fde51b87423
Source dataset
uspto-grants-2014_12
Patent number
US08906663B2

Linked notes

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