Atrolactic acid → (S)-Atrolactic acid

HRID 630576

Reaction equation

HRID 630576 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-a48db4f4a4084f93b5a92fa12d41073b
Source dataset
uspto-grants-2016_04
Patent number
US09315792B2

Linked notes

Loading…