Methanol → HCID 70511010, compound

HRID 2295967Notes

Reaction equation

HRID 2295967 reaction equation
O=[O+][O-].Cl[C@@H:5]1[N:8](C(=O)C(OCOC(=O)C(C)(C)C)=O)[C:7](=[O:22])[C@H:6]1[C:23]([OH:26])([CH3:25])[CH3:24].[C:27]([CH2:30][C:31](=[O:33])[CH3:32])(=[O:29])[CH3:28].CO.C[O-].[Na+]>ClCCl.CCCCCC.C(OCC)(=O)C>[C:27]([CH:30]([C:31](=[O:33])[CH3:32])[C@@H:5]1[NH:8][C:7](=[O:22])[C@@H:6]1[C:23]([OH:26])([CH3:24])[CH3:25])(=[O:29])[CH3:28]

Participants

8

Reactant 5

HCID 887MethanolHCID 24823OzoneHCID 31261AcetylacetoneHCID 10942334Sodium MethoxideHCID 86739189HCID 86739189, compound

Product 1

HCID 70511010HCID 70511010, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of 1.5 g (4 mMol) of pivaloyloxymethyl [3R,4S]-2-[4-chloro-3-(1-hydroxyisopropyl)-2-oxoazetidin-1-yl]-2-isopropylidenylacetate in 50 ml of dichloromethane is stirred at -78° C., to which is introduced ozone for 15 minutes. Consumption of the starting material is cofirmed by means of thin-layer chromatography. Introduction of nitrogen gas into the reaction mixture for 30 minutes gives a solution containing pivaloyloxymethyl [3R,4S]-2-[4-chloro-3-(1-hydroxyisopropyl)-2-oxoazetidin-1-yl]-2-oxoacetate. This solution is stirred at -10° C., to which are added 800 mg (8 mMol) of acetylacetone, then 20 ml of methanol dissolving 216 mg (4 mMol) of sodium methylate. The solvent is distilled off under reduced pressure, and the residue is stirred vigorously together with 20 ml of ethyl acetate, 1 ml of 1 N-hydrochloric acid and 10 ml of a saturated aqueous solution of sodium chloride. The organic layer is separated, dried over magnesium sulfate, and concentrated. The resulting reaction product is subjected to silica-gel column-chromatography (n-hexane-ethyl acetate 1:1-1:4). The fractions containing the desired product are combined and concentrated to give 80 mg of the titled compound as crystals, m.p. 109°-110° C.

Workup

  1. customConsumption of the starting material
  2. customIntroduction of nitrogen gas into the reaction mixture for 30 minutes gives a solution
  3. distillationThe solvent is distilled off under reduced pressure
  4. stirringthe residue is stirred vigorously together with 20 ml of ethyl acetate, 1 ml of 1 N-hydrochloric acid and 10 ml of a saturated aqueous solution of sodium chloride
  5. customThe organic layer is separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe resulting reaction product

Sources & evidence

ORD record
ord-fa46a663e08b4a2487800e41f9ac45e6
Source dataset
uspto-grants-1984_01
Patent number
US04427586

Reaction notes

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