Atrolactic acid → (S)-Atrolactic acid

HRID 1399485

Reaktionsgleichung

Reaktionsgleichung von HRID 1399485
[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

Komponenten

4

Edukt 3

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

Produkt 1

HCID 445144(S)-Atrolactic acid

Versuchsvorschrift

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.

Aufarbeitung

  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.

Quellen und Nachweise

ORD-Eintrag
ord-1c24f8bcb4bd47e8a9373fde51b87423
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906663B2

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