Boron trifluoride etherate → benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxylphenyl)propenyl]-beta-alaninate

HRID 264876Notes

Reaction equation

HRID 264876 reaction equation
[O:1]=[C:2]([NH:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])/[C:3](/[CH2:13][S:14][C:15](=[O:17])[CH3:16])=[CH:4]/[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.B(F)(F)F.CCOCC>C(Cl)Cl>[O:1]=[C:2]([NH:18][CH2:19][CH2:20][C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])/[C:3](/[CH2:13][S:14][C:15](=[O:17])[CH3:16])=[CH:4]\[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 8000Boron trifluoride etherateHCID 15287117benzyl N-(Z)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxyphenyl)propenyl]-beta-alaninate

Product 1

HCID 88378158benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxylphenyl)propenyl]-beta-alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.93 g (11.5 mmol) of the (Z) diester obtained in Example 17 (step D) are dissolved in 100 ml of methylene chloride which has been passed over basic alumina. The solution is irradiated for 2.5 h using a Hanovia TQ 150 lamp after having added dropwise 1.53 ml of boron trifluoride etherate solution (11.5 mmol). The solution is then washed with 1N hydrochloric acid solution (twice 80 ml), with saturated sodium hydrogen carbonate solution (twice 80 ml) and is dried over magnesium sulphate. After filtration and evaporation, 2.56 g of (E) isomer are recovered after flash chromatography.

Workup

  1. customThe solution is irradiated for 2.5 h
  2. washThe solution is then washed with 1N hydrochloric acid solution (twice 80 ml), with saturated sodium hydrogen carbonate solution (twice 80 ml)
  3. dry with materialis dried over magnesium sulphate
  4. filtrationAfter filtration and evaporation, 2.56 g of (E) isomer
  5. customare recovered after flash chromatography

Sources & evidence

ORD record
ord-72ee8b5247134143b2e3ef52c381437d
Source dataset
uspto-grants-1997_07
Patent number
US05646313

Reaction notes

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