HCID 21993066, compound → HCID 21993064, compound

HRID 1979105Notes

Reaction equation

HRID 1979105 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.   1 ⁢ H ⁢   ⁢ NMR ⁢   ⁢ ( 100 ⁢   ⁢ MHz , CDCl 3 ) ⁢ : ⁢   ⁢ δ =   ⁢ 1.25 ⁢   ⁢ ( s , 9 ⁢ H , C ⁡ ( CH 3 ) 3 ) ,   ⁢ 1.80 ⁢   ⁢ ( bs , 2 ⁢ H , NH 2 ) ,   ⁢ 3.95 ⁢   ⁢ ( s , 3 ⁢ H , OCH 3 ) ,   ⁢ 4.00 ⁢   ⁢ ( s , 2 ⁢ H , Ar ⁢ — ⁢ CH 2 ) ,   ⁢ 6.20 ⁢   ⁢ ( bs , 1 ⁢ H , SO 2 ⁢ NH ) ,   ⁢ 7.58 ⁢   ⁢ ( dd , 1 ⁢ H ; Ar—H ) ,   ⁢ 7.80 ⁢   ⁢ ( d , 1 ⁢ H , Ar—H ) ,   ⁢ 8.10 ⁢   ⁢ ( dd , 1 ⁢ H , Ar ⁢ — ⁢ H ) .

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-ae794b5f435a42e1bc7629efbee042b4
Source dataset
uspto-grants-2001_05
Patent number
US06239306B1

Reaction notes

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