Water → Florfenicol

HRID 507892ノート

反応式

HRID 507892 の反応式
[Cl:1][CH:2]([Cl:24])[C:3]([N:5]1[C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[O:7]C1(C)C)=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[Cl:24][CH:2]([Cl:1])[C:3]([NH:5][C@H:9]([CH2:10][F:11])[C@@H:8]([C:12]1[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][CH:17]=1)[OH:7])=[O:4]

参加物

5

反応物 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 68470341(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine

生成物 1

HCID 114811Florfenicol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
22.5 °C

実験手順

(4S,5R)-3-dichloroacetyl-2,2-dimethyl-4-fluoromethyl-5-[4-(methylsulfonyl)phenyl]-1,3-oxazolidine (Compound XIIIa) (60.5 g, 0.1519 moles) selectively hydrolyses in methylene chloride (300 mL) and water (100 mL) containing p-toluene sulfonic acid at 60° C. over several hours. Removal of the methylene chloride by distillation and cooling to 20-25° C. precipitates the product. Filtration, washing with water (100 mL) and toluene (100 mL) then drying yields (1R,2S)-2-dichloroacetamido-3-fluoro-1-[4-(methylsulfonyl)phenyl]-1-propanol (Florfenicol).

後処理

  1. customRemoval of the methylene chloride
  2. distillationby distillation
  3. customprecipitates the product
  4. filtrationFiltration
  5. washwashing with water (100 mL) and toluene (100 mL)
  6. customthen drying

出典と根拠

ORDレコード
ord-99953e722d6c4099858c77f508493564
出典データセット
uspto-grants-2010_08
特許番号
US07786329B2

反応ノート

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