Methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylate → Methyl cis-1-(2,4-Dimethoxybenzyl)-3-amino-4-oxoazetidine-2-carboxylate

HRID 127890Notes

Reaction equation

HRID 127890 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@H:8]([N:11]=[N+]=[N-])[C@@H:7]1[C:14]([O:16][CH3:17])=[O:15].[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@H:8]([NH2:11])[C@@H:7]1[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 2

HCID 86734328Methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 18632686Methyl cis-1-(2,4-Dimethoxybenzyl)-3-amino-4-oxoazetidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture containing 10.0 g (0.0312 mole) of methyl cis-1-(2,4-dimethoxybenzyl)-3-azido-4-oxoazetidine-2-carboxylate, 1.0 g of 10% palladium on carbon, and 200 ml of ethanol is hydrogenated for 2 hrs at 40°-45° and 60 psi of hydrogen. The reaction mixture is allowed to cool to 25° and is filtered through filter-aid. After removing the solvents in vacuo a clear, yellow gum of the title product is obtained.

Workup

  1. temperatureto cool to 25°
  2. filtrationis filtered
  3. filtrationthrough filter-aid
  4. customAfter removing the solvents in vacuo a clear, yellow gum of the title product
  5. customis obtained

Sources & evidence

ORD record
ord-64e715ff4f604f0084537a3117f4c2d2
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Reaction notes

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