Benzene → HCID 20070653, compound

HRID 1856361Notes

Reaction equation

HRID 1856361 reaction equation
[N+](C1C=CC=CC=1C[C:7](=O)[C:8]([O-:10])=[O:9])([O-])=O.O.[N+](C1C=CC=CC=1COC(N[C@H:27]1[C@H:30](CCOC(=O)C)[NH:29][C:28]1=[O:37])=O)([O-])=O.[CH:42]1C=CC=C[CH:43]=1>>[C:8]([O:10][CH2:42][CH2:43][N:29]1[CH2:30][CH2:27][C:28]1=[O:37])(=[O:9])[CH3:7]

Participants

5

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 6994219HCID 6994219, compoundHCID 70590894HCID 70590894, compound

Product 1

HCID 20070653HCID 20070653, compound

Procedure

The o-nitrobenzylglyoxylate, from Step B, is dissolved in 100 ml of benzene and refluxed using a Dean-Stark water separator containing 5 g of CaH2 for 0.5 hr; trans-3-[o-nitrobenzyloxycarbonylamino]-4-[2-acetoxyethyl]-2-azetidinone (3.51 g) is added and the mixture is refluxed for 6 hours, cooled and evaporated. The residue is chromatographed to give trans-1-(o-nitrobenzyloxycarbonylhydroxymethyl)-3-(o-nitrobenzyloxycarbonylamino)-4-(2-acetoxyethyl-2-azetidinone (3.8 g).

Workup

  1. temperaturerefluxed
  2. temperaturethe mixture is refluxed for 6 hours
  3. temperaturecooled
  4. customevaporated
  5. customThe residue is chromatographed

Sources & evidence

ORD record
ord-97b9d52f5e1644c4a52774c9afdf68f9
Source dataset
uspto-grants-1980_08
Patent number
US04218459

Reaction notes

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