Vinyl Acetate → HCID 56983398, compound

HRID 849378Notes

Reaction equation

HRID 849378 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]([OH:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C.[C:33](OC=C)(=[O:35])[CH3:34]>>[C:33]([O:11][C@@H:9]([C@H:8]([C:6]1[CH:5]=[CH:4][C:3]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:2]([F:1])[CH:7]=1)[CH2:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:10])(=[O:35])[CH3:34]

Participants

4

Reactant 3

HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 19591502HCID 19591502, compound

Product 1

HCID 56983398HCID 56983398, compound

Procedure

10.4 g of (2RS,3SR)-3-(2-fluoro-4-biphenylyl)-5-phenylpentan-2-ol was dissolved in 100 ml of vinyl acetate, and 4.3 ml of triethylamine was added. Then, 518 mg of immobilized lipase (Toyothium LIP) was added, followed by stirring at room temperature for 5 days. The enzyme was filtered off and 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 5.47 g of (2R,3S)-2-acetoxy-3-(2-fluoro-4-biphenylyl)-5-phenylpentane and 4.79 g of the above identified compound, respectively, as colorless oily substances. The absolute configuration of the above identified compound was determined by Mosher method (J. Am. Chem. Soc., vol. 113, p. 4092 (1991)).

Workup

  1. additionThen, 518 mg 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)

Sources & evidence

ORD record
ord-3f0d38e355c74af8987b4621097ae3d4
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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