HCID 53918863, compound → HCID 53653167, compound

HRID 465191Notes

Reaction equation

HRID 465191 reaction equation
[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C>CO.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[CH3:1][O:4][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 1

HCID 53918863HCID 53918863, compound

Product 1

HCID 53653167HCID 53653167, compoundYield 32.8%

Reagents, catalysts & solvents 2

HCID 11192Zinc AcetateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3 g of (3S,4S)-4-acetoxy-3-tritylamino-2-oxoazetidine in 30 ml of methanol is added 1.17 g of zinc acetate, and the mixture is refluxed for 30 minutes. The reaction mixture is concentrated under reduced pressure, followed by addition of ethyl acetate. The resulting insolubles are removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified on a silica-gel column (ethyl acetate: n-hexane=1:1) to give 0.912 g of (3S,4R)-4-methoxy-3-tritylamino-2-oxoazetidine.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. additionfollowed by addition of ethyl acetate
  4. customThe resulting insolubles are removed by filtration
  5. concentrationthe filtrate is concentrated under reduced pressure
  6. customThe residue is purified on a silica-gel column (ethyl acetate: n-hexane=1:1)

Sources & evidence

ORD record
ord-7bd7c8335af14dd68b05aad26c7a801b
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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