HCID 15281822, compound → HCID 15281825, compound

HRID 374496Notes

Reaction equation

HRID 374496 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[O:12][C:11]2=[O:27])=[CH:6][CH:5]=1)([O-])=O>[Zn].C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH:13]([CH2:15][O:16][C:17]3[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=3)[O:12][C:11]2=[O:27])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 15281822HCID 15281822, compound2×

Product 1

HCID 15281825HCID 15281825, compoundYield 108.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A 6.0 g quantity of zinc powder was added to an acetic acid (60 ml) solution of 3.0 g of methyl 4-[3-(4-nitrophenyl)-2-oxooxazolidin-5-yl]methoxybenzoate (compound 50) obtained in Example 3 at 60° C., and the mixture was stirred at the same temperature for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Ethanol was added to the obtained residue to collect the crystals by filtration. Thus, 3.0 g of the title compound (compound 112) was obtained in a quantitative yield.

Workup

  1. customobtained in Example 3 at 60° C.
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthanol was added to the obtained residue
  5. customto collect the crystals
  6. filtrationby filtration

Sources & evidence

ORD record
ord-e7e08a56110d4963a71c3b48c7017884
Source dataset
uspto-grants-1996_01
Patent number
US05480899

Reaction notes

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