1,1'-Carbonyldiimidazole → 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoate

HRID 235750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235750
[CH3:1][O:2][C:3]([C@H:6]1[C:9](=[O:10])[NH:8][C@@H:7]1[CH2:11][C:12]([OH:14])=O)([CH3:5])[CH3:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)(=[O:32])[CH2:28]C([O-])=O>O1CCCC1>[CH3:1][O:2][C:3]([C@H:6]1[C:9](=[O:10])[NH:8][C@@H:7]1[CH2:11][C:12](=[O:14])[CH2:28][C:27]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:32])([CH3:4])[CH3:5]

Komponenten

5

Edukt 3

HCID 682631,1'-CarbonyldiimidazoleHCID 18356643Propanedioic acid, mono[(4-nitrophenyl)methyl] esterHCID 566219192-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid

Produkt 1

HCID 867412794-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoateAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid (65.6 mg) in tetrahydrofuran (3.25 ml) was added carbonyldiimidazole (58.1 mg) at ambient temperature. After stirring for 6 hours at ambient temperature, magnesium salt of mono-p-nitrobenzyl malonate (179.7 mg) was added thereto and the resultant mixture was stirred overnight at ambient temperature. The solvent was distilled off and the residue was dissolved in ethyl acetate (10 ml) and filtered. The filtrate was washed in turn with 1N hydrochloric acid, water, 10% aqueous sodium bicarbonate, water, 5% aqueous citric acid, water and a saturated aqueous sodium chloride. After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated in vacuo. The residue (101.2 mg) was chromatographed on silica gel (2 g) eluting with a mixture of methylene chloride and acetone (80:1 to 4:1) to give 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methyl-ethyl)-4-oxoazetidin-2-yl] -3-oxobutanoate (71.0 mg) as an amorphous solid.

Aufarbeitung

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed in turn with 1N hydrochloric acid, water, 10% aqueous sodium bicarbonate, water, 5% aqueous citric acid, water
  5. dry with materialAfter drying over magnesium sulfate
  6. extractionthe ethyl acetate extract
  7. filtrationwas filtered
  8. customevaporated in vacuo
  9. customThe residue (101.2 mg) was chromatographed on silica gel (2 g)
  10. washeluting with a mixture of methylene chloride and acetone (80:1 to 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-54e7287f06e54dab92c48cd243024e28
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640915

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