HCID 21993066, compound → HCID 21993064, compound

HRID 582583Notes

Reaction equation

HRID 582583 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][N:16]=[N+]=[N-])[CH:12]=[CH:11][C:10]=1[C:19]([O:21][CH3:22])=[O:20])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[C:13]([CH2:15][NH2:16])[CH:12]=[CH:11][C:10]=1[C:19]([O:21][CH3:22])=[O:20])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 21993066HCID 21993066, compound

Product 1

HCID 21993064HCID 21993064, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

16.3 g (50 mmol) of N-tert-butyl-5-azidomethyl-2-methoxycarbonylbenzenesulfonamide are dissolved in 300 ml of methanol and hydrogenated over Pd/C (5%). The mixture is filtered and evaporated to dryness. The crude product obtained is purified by elution through a silica gel column using ethyl acetate/methanol 4:1. 11.2 g (74%) of N-tert-butyl-5-aminomethyl-2-methoxycarbonylbenzenesulfonamide are obtained as a viscous oil.

Workup

  1. filtrationThe mixture is filtered
  2. customevaporated to dryness
  3. customThe crude product obtained
  4. customis purified by elution through a silica gel column

Sources & evidence

ORD record
ord-bc3dc8446157450ab6bb121ca880f304
Source dataset
uspto-grants-1999_07
Patent number
US05925597

Reaction notes

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