Methyl2-(2,3,4-trifluoroanilino)propionate → (2S)-2-(2,3,4-trifluoroanilino)propionic acid
Reaction equation
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]([CH3:10])[C:6]([O:8]C)=[O:7]>P([O-])([O-])([O-])=O>[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[CH:12]=[CH:11][C:3]=1[NH:4][C@@H:5]([CH3:10])[C:6]([OH:8])=[O:7]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Microbial cells (IFO-1575; Zygoascus hellenicus) were cultured in an MY medium (pH 6.0; 50 ml) at 30° C. for 48 hours. Methyl 2-(2,3,4-trifluoroanilino)propionate (1.0 g) was suspended in a 0.1 M phosphate buffer solution (pH 6.5; 90 ml). Then the above-described liquid culture (10 ml) was added thereto and gently stirred. The mixture was stirred for additional 16 hours while maintaining at 30° C. Then it was treated as in Example 43 to thereby give methyl (2R)-2-(2,3,4-trifluoroanilino) propionate (0.39 g, optical purity 91% ee) and the title compound (0.45 g, optical purity 84% ee).
Workup
- additionThen the above-described liquid culture (10 ml) was added
- stirringThe mixture was stirred for additional 16 hours
Sources & evidence
- ORD record
- ord-ca5c05ce341d431d955212c0e5c0fdc8
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07189847B2
Reaction notes
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