Vinyl Acetate → (2R,3S)-2-acetoxy-3-(4-phenoxyphenyl)-5-phenylpentane

HRID 849365ノート

反応式

HRID 849365 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]([OH:17])[CH3:16])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:33](OC=C)(=[O:35])[CH3:34]>>[C:33]([O:17][C@@H:15]([C@H:14]([C:11]1[CH:12]=[CH:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH3:16])(=[O:35])[CH3:34]

参加物

4

反応物 3

HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 19591495(2RS,3SR)-3-(4-phenoxyphenyl)-5-phenylpentan-2-ol

生成物 1

HCID 57004388(2R,3S)-2-acetoxy-3-(4-phenoxyphenyl)-5-phenylpentane

反応条件

温度
30 °C

実験手順

47.2 g of (2RS,3SR)-3-(4-phenoxyphenyl)-5-phenylpentan-2-ol was dissolved in 470 ml of vinyl acetate, and 19.4 ml of triethylamine was added. Then, 4.7 g of immobilized lipase (Toyothium LIP) was added, followed by stirring at 30° C. for 2 days. The enzyme was filtered off and then, washed with ethyl acetate. The filtrate and the washing liquid were put together, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1) to obtain 23.8 g of (2R,3S)-2-acetoxy-3-(4-phenoxyphenyl)-5-phenylpentane and 22.2 g of the above identified compound, respectively, as colorless oily substances. Further, the absolute configuration of the above-identified compound was determined by Mosher method (J. Am. Chem. Soc., vol. 113, p. 4092 (1991)).

後処理

  1. additionThen, 4.7 g of immobilized lipase (Toyothium LIP) was added
  2. filtrationThe enzyme was filtered off
  3. washwashed with ethyl acetate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1)

出典と根拠

ORDレコード
ord-5962060bad7c45b8a6a5acb63badc035
出典データセット
uspto-grants-2000_01
特許番号
US06011174

反応ノート

読み込み中…