Acetic Anhydride → (S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol

HRID 2256471

反応式

HRID 2256471 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:14])([CH2:12][OH:13])[CH2:10]O.CC(O)C[CH2:18][CH:19]([OH:21])C.C(OC(=O)C)(=[O:25])C>O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:14])([CH3:10])[C@H:12]([O:13][C:19](=[O:21])[CH3:18])[OH:25]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 180492,5-HexanediolHCID 112179522-(2,4-Difluorophenyl)-1,2,3-propanetriol

生成物 1

HCID 53684152(S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
30 °C

実験手順

A 300 ml reaction vessel was charged with 5 g of 2-(2,4-difluorophenyl)-1,2,3-propanetriol, 100 ml of diisopropanol, 2.45 ml of acetic anhydride and 5 g of Novozym 435 made by NOVO NORDISK, Ltd. (derived from Candida antarctica, Enzyme No. 24). The resulting mixture was stirred at 30° C. for 15 hours. After 10 ml of water was added thereto, the reaction liquid was filtered to remove the enzyme. An organic layer of the filtrate was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1) to give 1 g of (S)-2-(2,4-difluorophenyl)-1-acetoxy-1,2-propanediol. The optical purity thereof was 8% ee.

後処理

  1. customA 300 ml reaction vessel
  2. customthe reaction liquid
  3. filtrationwas filtered
  4. customto remove the enzyme
  5. dry with materialAn organic layer of the filtrate was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-1a106bed788d4ceb8099cc1514a28815
出典データセット
uspto-grants-1997_08
特許番号
US05654472

関連ノート

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