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

HRID 563199

反応式

HRID 563199 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 67006383(2R,3S)-2-(3-chloro-4-cyano-2-ethylphenylamino)-3-hydroxybutanoic acid収率 467.3%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c445dec7a86d4f418e70efbb44377c47
出典データセット
uspto-grants-2011_11
特許番号
US08067448B2

関連ノート

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