Phosphorus pentachloride → 3-(2-Hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone

HRID 2418197Notes

Reaction equation

HRID 2418197 reaction equation
[NH2:1][CH:2]1[CH2:5][N:4]([CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]1=[O:18].C[Si](C([Si](C)(C)C)C(N)=O)(C)C.ClC(Cl)C([O:35][N:36]=[C:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38](O)=[O:39])=O.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:35][N:36]=[C:37]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:38]([NH:1][CH:2]1[CH2:5][N:4]([CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][C:8]([O:10][CH3:11])=[O:9])[C:3]1=[O:18])=[O:39]

Participants

7

Reactant 5

HCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 11708267BistrimethylsilylacetamidHCID 53748477HCID 53748477, compoundHCID 539654873-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone

Product 1

HCID 867370493-(2-Hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinoneYield 35.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Amino-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (1.3 g.) was added to methylene chloride (30 ml.), and then bis(trimethylsilyl)acetamide (3.05 g.) was added thereto. To the solution, there was dropwise added methylene chloride (30 ml.) solution containing 2-(2,2-dichloroacetoxyimino)-2-phenylacetic acid (1.9 g.) and phosphorus pentachloride (1.7 g.) at -40° to -35° C. in the course of 5 minutes. The mixture was stirred at the same temperature for 15 minutes and additionally stirred at 5° C. for 15 minutes. An aqueous sodium bicarbonate was added to the reaction mixture and the mixture was stirred at ambient temperature for 5 minutes. The methylene chloride layer was separated from the mixture, washed with dilute hydrochloric acid, an aqueous sodium bicarbonate and water in turn, and then dried over magnesium sulfate. The solvent was removed by distillation under reduce pressure to give a residue, which was subjected to column chromatography on silica gel (100 g.). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solvent was distilled off from the eluate under reduced pressure to give crystals of 3-(2-hydroxyimino-2-phenylacetamido)-1-(2-methoxycarbonyl-1-phenylethyl)-2-azetidinone (0.74 g.).

Workup

  1. stirringadditionally stirred at 5° C. for 15 minutes
  2. stirringthe mixture was stirred at ambient temperature for 5 minutes
  3. customThe methylene chloride layer was separated from the mixture
  4. washwashed with dilute hydrochloric acid
  5. dry with materialan aqueous sodium bicarbonate and water in turn, and then dried over magnesium sulfate
  6. customThe solvent was removed by distillation
  7. customto give a residue, which
  8. washElution
  9. additionthe fractions containing a desired compound
  10. customwere collected
  11. distillationThe solvent was distilled off from the eluate under reduced pressure

Sources & evidence

ORD record
ord-64f62ea953724f46aeb8eda15ed6c1a2
Source dataset
uspto-grants-1984_09
Patent number
US04472300

Reaction notes

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