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 1719306Notes

Reaction equation

HRID 1719306 reaction equation
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]

Participants

6

Reactant 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

Product 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-enoateYield 111.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9673b6e0c77246418737b0e2a099b470
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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