Tin atom → HCID 18542590, compound

HRID 1268216Notes

Reaction equation

HRID 1268216 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:20]([C:21](=[O:23])[NH2:22])=[CH:19][C:18]([N+:24]([O-])=O)=[CH:17][C:16]=2[Cl:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Sn]>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[C:20]([C:21](=[O:23])[NH2:22])=[CH:19][C:18]([NH2:24])=[CH:17][C:16]=2[Cl:27])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5352426Tin atomHCID 18542597HCID 18542597, compound

Product 1

HCID 18542590HCID 18542590, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-5-carbamoyl-3-chloronitrobenzene (2.2 g) in acetic acid (100 ml) was added tin powder (9.9 g) and the mixture was stirred at room temperature for 11 hours. The reaction mixture was filtered through Celite (trade mark) and the filtrate was concentrated in vacuo. The residual pale yellow solid was dissolved in aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered and the filtrate concentrated in vacuo to give the desired compound (1.7 g, yield 83%) as a yellow amorphous solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite (trade mark)
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residual pale yellow solid was dissolved in aqueous potassium carbonate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-ca8b07c2442a4247a71f726e03e64f30
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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