Vinyl Acetate → HCID 15458176, compound

HRID 1602577Notes

Reaction equation

HRID 1602577 reaction equation
[OH:1][CH:2]([CH3:24])[CH:3]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.[C:32](OC=C)(=[O:34])[CH3:33]>>[C:32]([O:1][C@H:2]([CH3:24])[C@H:3]([C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=1)(=[O:34])[CH3:33].[OH:1][C@@H:2]([CH3:24])[C@@H:3]([C:15]1[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=1)[CH2:4][C:5]1[O:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 19364506ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate

Product 2

HCID 15458176HCID 15458176, compoundHCID 70110078HCID 70110078, compound

Procedure

6.35 g of ethyl 5-{(2RS,3SR)-3-hydroxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate [the compound prepared in Reference Example 4(2)] was dissolved in 64 ml of vinyl acetate, and 2.66 ml of triethylamine was added. Then, 635 mg of immobilized lipase (Toyothium LIP) was added, and the reaction solution was stirred at room temperature for 5 days. The insolubles were filtered off, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=7/2→2/1] to give 2.93 g of ethyl 5-{(2S,3R)-3-acetoxy-2-(4-nitrophenyl)butyl}-2-furancarboxylate and 2.81 g of the title compound as colorless oily substances, respectively. The absolute steric configuration of the title compound was determined by the Mosher method (J.Am.Chem.Soc.), vol. 113, p. 4092 (1991)).

Workup

  1. additionThen, 635 mg of immobilized lipase (Toyothium LIP) was added
  2. filtrationThe insolubles were filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography [hexane/ethyl acetate=7/2→2/1]

Sources & evidence

ORD record
ord-5fc57ea66ea540ba9230221957851687
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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