tert-Butanol → HCID 15592328, compound

HRID 2418202Notes

Reaction equation

HRID 2418202 reaction equation
C([CH:4]([N:8]1[CH2:11][CH:10]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]1=[O:22])[CH:5]([CH3:7])[CH3:6])(O)=O.C([N:25]([CH2:28]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:37])C=CC=CC=1.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[C:47]([O:51][C:28]([NH:25][CH:4]([N:8]1[CH2:11][CH:10]([NH:12][C:13](=[O:21])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:22])[CH:5]([CH3:6])[CH3:7])=[O:37])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 13859055HCID 13859055, compound

Product 1

HCID 15592328HCID 15592328, compound

Procedure

A mixture of 1-(1-carboxy-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (1.50 g), triethylamine (0.51 g), diphenylphosphoryl azide (1.4 g) and tert-butyl alcohol (30 ml) was heated gradually, and refluxed under heating for 5 hours. After the reaction, the tert-butyl alcohol was removed by distillation from the reaction mixture under reduced pressure to give a residue, which was subjected to column chromatography on silica gel. Elution was carried out with a mixture of benzene and ethyl acetate, and the fractions containing a desired compound were collected. The eluate was evaporated to dryness under reduced pressure to give 1-(1-tert-butoxycarbonylamino-2-methylpropyl)-3-(2-phenylacetamido)-2-azetidinone (1.1 g), mp 64° to 66° C.

Workup

  1. temperaturewas heated gradually
  2. temperaturerefluxed
  3. temperatureunder heating for 5 hours
  4. customAfter the reaction
  5. customthe tert-butyl alcohol was removed by distillation from the reaction mixture under reduced pressure
  6. customto give a residue, which
  7. washElution
  8. additionwas carried out with a mixture of benzene and ethyl acetate
  9. additionthe fractions containing a desired compound
  10. customwere collected
  11. customThe eluate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c933438053d54b4e91545a325c3f8d0f
Source dataset
uspto-grants-1984_09
Patent number
US04472300

Reaction notes

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