HCID 21993066, compound → HCID 21993064, compound

Participants

Reaction Steps

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 ) .

Provenance & Evidence