1,1'-Carbonyldiimidazole → 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoate

HRID 235750Notes

Reaction equation

HRID 235750 reaction equation
[CH3:1][O:2][C:3]([C@H:6]1[C:9](=[O:10])[NH:8][C@@H:7]1[CH2:11][C:12]([OH:14])=O)([CH3:5])[CH3:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)(=[O:32])[CH2:28]C([O-])=O>O1CCCC1>[CH3:1][O:2][C:3]([C@H:6]1[C:9](=[O:10])[NH:8][C@@H:7]1[CH2:11][C:12](=[O:14])[CH2:28][C:27]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=1)=[O:32])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 18356643Propanedioic acid, mono[(4-nitrophenyl)methyl] esterHCID 566219192-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid

Product 1

HCID 867412794-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidine-2-yl]-3-oxobutanoateYield 57.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(2R, 3S)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid (65.6 mg) in tetrahydrofuran (3.25 ml) was added carbonyldiimidazole (58.1 mg) at ambient temperature. After stirring for 6 hours at ambient temperature, magnesium salt of mono-p-nitrobenzyl malonate (179.7 mg) was added thereto and the resultant mixture was stirred overnight at ambient temperature. The solvent was distilled off and the residue was dissolved in ethyl acetate (10 ml) and filtered. The filtrate was washed in turn with 1N hydrochloric acid, water, 10% aqueous sodium bicarbonate, water, 5% aqueous citric acid, water and a saturated aqueous sodium chloride. After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated in vacuo. The residue (101.2 mg) was chromatographed on silica gel (2 g) eluting with a mixture of methylene chloride and acetone (80:1 to 4:1) to give 4-nitrobenzyl 4-[(2R, 3S)-3-(1-methoxy-1-methyl-ethyl)-4-oxoazetidin-2-yl] -3-oxobutanoate (71.0 mg) as an amorphous solid.

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in ethyl acetate (10 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed in turn with 1N hydrochloric acid, water, 10% aqueous sodium bicarbonate, water, 5% aqueous citric acid, water
  5. dry with materialAfter drying over magnesium sulfate
  6. extractionthe ethyl acetate extract
  7. filtrationwas filtered
  8. customevaporated in vacuo
  9. customThe residue (101.2 mg) was chromatographed on silica gel (2 g)
  10. washeluting with a mixture of methylene chloride and acetone (80:1 to 4:1)

Sources & evidence

ORD record
ord-54e7287f06e54dab92c48cd243024e28
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

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