Potassium Carbonate → (2R,3S)-2-(3-chloro-4-cyano-2-ethylphenylamino)-3-hydroxybutanoic acid

HRID 1254648

Reaktionsgleichung

Reaktionsgleichung von HRID 1254648
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[C:3]=1[CH2:11][CH3:12].[NH2:13][C@@H:14]([C:18]([OH:20])=[O:19])[C@H:15]([CH3:17])[OH:16].C(=O)([O-])[O-].[K+].[K+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.CS(C)=O>[Cl:10][C:4]1[C:3]([CH2:11][CH3:12])=[C:2]([NH:13][C@H:14]([C@@H:15]([OH:16])[CH3:17])[C:18]([OH:20])=[O:19])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 69435D-ThreonineHCID 579086952-Chloro-3-ethyl-4-fluorobenzonitrile

Produkt 1

HCID 67006383(2R,3S)-2-(3-chloro-4-cyano-2-ethylphenylamino)-3-hydroxybutanoic acidAusbeute 467,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

4-Fluoro-2-chloro-3-ethyl benzonitrile (1.0 g, 5.45 mmol), D-threonine (779 mg, 6.54 mmol), potassium carbonate (1.51 g, 10.9 mmol) and DMSO (6 mL) were heated at 85° C. for 17.5 h. The reaction mixture was allowed to cool to room temperature whereupon water (20 mL) was added followed by citric acid monohydrate (2 g). After stirring for 10 min the mixture was partitioned between EtOAc (40 mL) and water. The organic phase was then washed with water (15 mL), brine (15 mL), dried (Na2SO4) and concentrated to furnish a pale yellow solid (7.2 g). This crude product was then passed through a silica-plug [hexanes-EtOAc (95:5) as eluent] to furnish a white solid (928 mg), which was used directly in the next step.

Aufarbeitung

  1. additionwas added
  2. customwas partitioned between EtOAc (40 mL) and water
  3. washThe organic phase was then washed with water (15 mL), brine (15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fc173d41374b4fc4bdab29c1344b3928
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455525B2

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