Atrolactic acid → (S)-Atrolactic acid

HRID 2111504Notes

Reaction equation

HRID 2111504 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-e7a7773fc4774166a726df16c81889c8
Source dataset
uspto-grants-2009_04
Patent number
US07521216B2

Reaction notes

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