645-96-5 → HCID 22825976, compound

HRID 622585Notes

Reaction equation

HRID 622585 reaction equation
C(O[CH:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:20])[CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=O)C.C1C=CC([Se])=CC=1>C(Cl)Cl.B(F)(F)F.CCOCC.C(OCC)(=O)C>[O:13]([CH2:12][C:11]([NH:10][C@H:6]1[CH2:5][NH:8][C:7]1=[O:9])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 6327608645-96-5HCID 13182458HCID 13182458, compound

Product 1

HCID 22825976HCID 22825976, compound

Reagents, catalysts & solvents 3

HCID 8000Boron trifluoride etherateCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, 4-(R,S)-acetoxy-3-(S)-(phenoxyacetamido)azetidinone (1.32 g, 4.74 mmol) was dissolved in methylene chloride (9 ml). To this solution was added phenylselenol (1.5 ml, approximately 9.8 mmol), then boron trifluoride-etherate (10 drops). The resultant solution was stirred at room temperature for 20 minutes. The solution was diluted with ethyl acetate and extracted with saturated aqueous sodium bicarbonate solution (2×). The solution was dried over magnesium sulfate, filtered and concentrated in vacuo. The concentrate was absorbed onto silica gel (7 g) and then chromatographed over an additional amount of silica gel (15 g) using a gradient elution of toluene to ethyl acetate. The product-containing fractions gave 4-(R,S)-phenylselenyl)-3-(S)-(phenoxyacetamido)azetidinone.

Workup

  1. extractionextracted with saturated aqueous sodium bicarbonate solution (2×)
  2. dry with materialThe solution was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe concentrate was absorbed onto silica gel (7 g)
  6. customchromatographed over an additional amount of silica gel (15 g)
  7. washa gradient elution of toluene to ethyl acetate

Sources & evidence

ORD record
ord-683e05ed95fc4f47b1ea831de4a93909
Source dataset
uspto-grants-1988_09
Patent number
US04771135

Reaction notes

Loading…