Water → 3-Phenyllactic acid, (S)-

HRID 1170815Notes

Reaction equation

HRID 1170815 reaction equation
B(F)(F)F.CO.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:20]1([CH2:26][CH:27]([OH:31])[C:28]([OH:30])=[O:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(Cl)Cl.FC(F)(F)C(OC(=O)C(F)(F)F)=O>[CH:23]1[CH:22]=[CH:21][C:20]([CH2:26][C@H:27]([OH:31])[C:28]([OH:30])=[O:29])=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 3848(+-)-3-Phenyllactic acidHCID 9845Trifluoroacetic anhydride2×HCID 11062313Boron, trifluoro(methanol)-, (T-4)-

Product 1

HCID 4447183-Phenyllactic acid, (S)-

Reagents, catalysts & solvents 2

HCID 9845Trifluoroacetic anhydrideCatalystHCID 6344DichloromethaneSolvent

Procedure

The derivatization was carried out with BF3-methanol (see above) or with trifluoroacetic anhydride. For the derivatization with trifluoroacetic anhydride, 5 mg of 3-phenyllactic acid were dissolved in 500 μl of CH2Cl2, treated with 5 drops of trifluoroacetic anhydride, shaken for 1 minute at room temperature and subsequently treated with approximately 500 μl of H2O. The organic phase is dried over Na2SO4, and the samples were then measured by GC on a chiral column.

Workup

  1. dry with materialThe organic phase is dried over Na2SO4

Sources & evidence

ORD record
ord-fc6823cfcf554a83995871ed76005191
Source dataset
uspto-grants-2010_11
Patent number
US07829324B2

Reaction notes

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