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Acetone → methyl 2-{(3R,4R)-3-isocyano-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl}-3-methylbut-2-enoate

HRID 1719321
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1719321
[N+:1]([C@@H:3]1[C@@H:6]([CH2:7][CH:8]=[CH2:9])[N:5]([C:10](=[C:15]([CH3:17])[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[C:4]1=[O:18])#[C-:2].C([Li])CCC.[CH3:24][C:25]([CH3:27])=[O:26].Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:30]>O1CCCC1.C(O)(=O)C>[N+:1]([C@@:3]1([C:25]([CH3:27])([O:26][C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])[CH3:24])[C@@H:6]([CH2:7][CH:8]=[CH2:9])[N:5]([C:10](=[C:15]([CH3:17])[CH3:16])[C:11]([O:13][CH3:14])=[O:12])[C:4]1=[O:18])#[C-:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 180AcetoneHCID 782054-Nitrobenzyl chloroformateHCID 54071546methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoateHCID 178418339Butyllithium

Produkt 1

HCID 53687939methyl 2-{(3R,4R)-3-isocyano-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl}-3-methylbut-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (127.6 mg) in tetrahydrofuran (2.55 ml) was added dropwise a solution of n-butyl lithium (0.409 ml of 1.51M solution in hexane) at -78° C. over a period of 3 minutes. After stirring for 15 minutes at -78° C., the reaction mixture was added dropwise with a solution of acetone (0.0459 ml) in tetrahydrofuran (0.459 ml) at -78° C. over a period of 3 minutes. After stirring for 25 minutes at -78° C., the reaction mixture was added dropwise with a solution of 4-nitrobenzyl chloroformate (124.1 mg) in tetrahydrofuran (1.24 ml) at -78° C. over a period of 3 minutes. The resulting solution was allowed to warm to 0° C. over a period of 40 minutes and added with acetic acid (0.0412 ml) at 0° C. The solvent was distilled off in vacuo at 0° C. and the residue was dissolved in ethyl acetate (30 ml) and washed with brine, aqueous sodium bicarbonate, brine and saturated aqueous sodium chloride. After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated in vacuo. The residual oil (285.4 mg) was chromatographed on silica gel (5.7 g) eluting with a mixture of ethyl acetate and hexane (1:5→1:3) to give methyl 2-{(3R,4R)-3-isocyano-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl}-3-methylbut-2-enoate (211.2 mg) as an oil.

Aufarbeitung

  1. stirringAfter stirring for 25 minutes at -78° C.
  2. temperatureto warm to 0° C. over a period of 40 minutes
  3. distillationThe solvent was distilled off in vacuo at 0° C.
  4. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  5. washwashed with brine, aqueous sodium bicarbonate, brine and saturated aqueous sodium chloride
  6. dry with materialAfter drying over magnesium sulfate
  7. extractionthe ethyl acetate extract
  8. filtrationwas filtered
  9. customevaporated in vacuo
  10. customThe residual oil (285.4 mg) was chromatographed on silica gel (5.7 g)
  11. washeluting with a mixture of ethyl acetate and hexane (1:5→1:3)

Quellen und Nachweise

ORD-Eintrag
ord-7cb938d6c08c4fcb875748ac33ea48de
Quelldatensatz
uspto-grants-1985_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04539152

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