1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoate

HRID 1719306Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719306
N12CCCN=C1CCCCC2.[OH:12][C:13]([C@:16]1([N+:32]#[C-:33])[C@@H:19]([CH2:20][CH:21]=[CH2:22])[N:18]([C:23](=[C:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[C:17]1=[O:31])([CH3:15])[CH3:14]>C(Cl)Cl.CC(C)=O.C(O)(=O)C>[CH2:20]([C@@H:19]1[C@:16]2([N:32]=[CH:33][O:12][C:13]2([CH3:14])[CH3:15])[C:17](=[O:31])[N:18]1[C:23](=[C:28]([CH3:30])[CH3:29])[C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH2:22]

Komponenten

6

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53962359methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

Produkt 1

HCID 22823197methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoateAusbeute 111,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 180AcetoneLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (17 μl) in methylene chloride (0.1 ml) was added to a solution of methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (17 mg) in methylene chloride (1 ml) and acetone (1 ml) at 0° C., and the mixture was stirred for 20 hours at ambient temperature. Acetic acid (2 drops) was added to the reaction mixture at 0° C., and the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate (20 ml), and the solution was washed with 10% aqueous phosphoric acid, brine, phosphate buffer (pH 6.9), aqueous sodium bicarbonate and brine, dried over magnesium sulfate and evaporated in vacuo to give methyl 2-[(3R,4R)-3-allyl-5,5-dimethyl-1-oxo-2,8-diaza-6-oxaspiro[3,4]oct-7-en-2-yl]-3-methylbut-2-enoate (19 mg) as crude crystals.

Aufarbeitung

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  3. washthe solution was washed with 10% aqueous phosphoric acid, brine, phosphate buffer (pH 6.9), aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9673b6e0c77246418737b0e2a099b470
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539152

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