Boron trifluoride etherate → HCID 86736406, compound

HRID 614451Notes

Reaction equation

HRID 614451 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@H:12]1[C:15](=[O:16])[NH:14][C@H:13]1[CH2:17][I:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[O:21].B(F)(F)F.CCOCC>O1CCCC1>[O:1]([CH2:8][C:9]([NH:11][C@H:12]1[C:15](=[O:16])[N:14]([CH:20]([OH:21])[C:19]([O:23][CH3:24])=[O:22])[C@H:13]1[CH2:17][I:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 70604956HCID 70604956, compound

Product 1

HCID 86736406HCID 86736406, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.360 g (1.0 mmol) of cis-3-phenoxyacetamido-4-oxo-2-azetidinylmethyl iodide, 0.440 g (5.0 mmol) of methyl glyoxylate, and 246 μl (2.0 mmol) of boron trifluoride etherate in 10 ml of anhydrous tetrahydrofuran is stirred at ambient temperature under an argon atmosphere for 5 hours. At this time 123 μl (1.0 mmol) of boron trifluoride etherate is added and the mixture is stirred for an additional 2 hours. The tetrahydrofuran is removed in vacuo and the residue is taken up in ethyl acetate and extracted with aqueous NaHCO3 and brine. The ethyl acetate solution is dried, filtered and evaporated to give 0.350 g of crude product which is purified by preparative thin-layer chromatography (silica gel GF); 0.174 g of pure product.

Workup

  1. customThe tetrahydrofuran is removed in vacuo
  2. extractionextracted with aqueous NaHCO3 and brine
  3. dry with materialThe ethyl acetate solution is dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-97fe3bdfcd034915b84deec8d46583ce
Source dataset
uspto-grants-1979_03
Patent number
US04144333

Reaction notes

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