Methyl (2R)-2-(2,3,4-trifluoroanilino)propionate → (2S)-2-(2,3,4-trifluoroanilino)propionic acid

HRID 8450

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].FC1C(F)=C(F)C=CC=1N[C@H](C)C(OC)=O>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

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-636e813181f848728e478a98a7f62007
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087778B2

Linked notes

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