Ethyl 2-methylacetoacetate → HCID 70511822, compound

HRID 2295969Notes

Reaction equation

HRID 2295969 reaction equation
[CH3:1][O-:2].[Na+].C[CH:5]([C:11]([CH3:13])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[C@H]1[N:18](C(=O)C(OC)=O)[C:17](=[O:25])[C@@H:16]1[N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].Cl[CH2:38]Cl>C(O)(=O)C>[C:1]([CH:9]([O:8][C:6]([CH2:5][CH2:11][C@H:13]1[NH:18][C:17](=[O:25])[C@@H:16]1[N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36])=[O:7])[CH3:10])(=[O:2])[CH3:38]

Participants

6

Reactant 4

HCID 701Ethyl 2-methylacetoacetateHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 13255224HCID 13255224, compound

Product 1

HCID 70511822HCID 70511822, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Procedure

To 10 ml of 0.2 M methanolic sodium methoxide cooled at -78° C., are added dropwise a solution of 864 mg of ethyl 2-methylacetoacetate and 672 mg (2 mMol) of methyl [3S,4R]-2-(4-chloro-3-phthalimido-2-oxoazetidin-1-yl)-2-oxoacetate in 5 ml of dichloromethane. After 3 min, 10 drops of acetic acid are added to the reaction mixture. The solvent is evaporated and the residue is taken into ethyl acetate, washed with water and dried over anhydrous magnesium sulfate. The solution is evaporated to dryness, the residue is subjected to silica-gel column chromatography (silica gel, 30 g) and developed with n-hexane-ethyl acetate (1:2). The fractions containing the desired compound are combined and concentrated, and the residue is triturated with ether to afford 200 mg of the titled compound. m.p. 135°-145° C.

Workup

  1. customThe solvent is evaporated
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solution is evaporated to dryness
  5. additionThe fractions containing the desired compound
  6. concentrationconcentrated
  7. customthe residue is triturated with ether

Sources & evidence

ORD record
ord-f4471886768846889409b122de114229
Source dataset
uspto-grants-1984_01
Patent number
US04427586

Reaction notes

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