Benzene → HCID 86736765, compound

HRID 2051700Notes

Reaction equation

HRID 2051700 reaction equation
C([CH:3]1[N:6]([CH:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([O:10][CH3:11])=[O:9])[C:5](=[O:18])[CH:4]1[N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])=O.[CH2:30]([O:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[CH:39]1C=CC=CC=1>>[CH2:30]([O:37][N:38]=[C:3]1[N:6]([CH:7]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]([O:10][CH3:11])=[O:9])[C:5](=[O:18])[C:4]1([CH3:39])[N:19]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 102313O-BenzylhydroxylamineHCID 20243610HCID 20243610, compound

Product 1

HCID 86736765HCID 86736765, compound

Procedure

Methyl 2-(4-formyl-2-oxo-3-phthalimido-1-azetidinyl)-2-phenylacetate (390 mg.) and O-benzyl hydroxylamine (170 mg.) were dissolved in dried benzene (10 ml), and the solution was stirred at ambient temperature for 4 hours and then heated at 50° to 60° C. for an hour. The reaction mixture was washed with 1% hydrochloric acid (10 ml.), water and an aqueous sodium chloride and then dried over magnesium sulfate. The solution was evaporated to dryness under reduced pressure to give a residue (560 mg.), which was subjected to column chromatography on silica gel (15 g.). Elution was carried out with chloroform and the fractions containing a desired compound were collected. The solution was removed by distillation from the solution under reduced pressure to give methyl 2-(4-benzyloxyimino-methyl-2-oxo-3-phthalimido-1-azetidinyl)-2-phenylacetate (530 mg.).

Workup

  1. temperatureheated at 50° to 60° C. for an hour
  2. washThe reaction mixture was washed with 1% hydrochloric acid (10 ml.), water
  3. dry with materialan aqueous sodium chloride and then dried over magnesium sulfate
  4. customThe solution was evaporated to dryness under reduced pressure
  5. customto give a residue (560 mg.), which
  6. washElution
  7. additionthe fractions containing a desired compound
  8. customwere collected
  9. customThe solution was removed by distillation from the solution under reduced pressure

Sources & evidence

ORD record
ord-338ef14a3874469c9c4d36575a646e43
Source dataset
uspto-grants-1980_01
Patent number
US04181800

Reaction notes

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