반응 #86608

반응 방정식

[3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide

N-(tert-butoxycarbonyl)-N-methylglycine

N,N-diisopropylethylamine

1-hydroxybenzotriazole hydrate

1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

title compound

수율 77.4%

N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide

수율 77.4%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The reaction was isolated
2. 2
   세척by washing with aqueous NaHCO3 and water
3. 3
   기타to give crude product that
4. 4
   기타was purified on a silica gel column
5. 5
   세척eluting with 5-10% 1 M NH3 in methanol and methylene chloride

실험 절차

N-(tert-butoxycarbonyl)-N-methylglycine (309 mg, 1.63 mmol) was taken up in methylene chloride (7.8 mL) and treated with N,N-diisopropylethylamine (1.0 mL, 5.7 mmol), and 1-hydroxybenzotriazole hydrate (233 mg, 1.52 mmol). After 10 minutes at room temperature, [3-(methylamino)propyl](triphenyl)phosphonium bromide hydrobromide (933 mg, 1.88 mmol) was added, followed by 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (353 mg, 1.84 mmol) and 4-dimethylaminopyridine (145 mg, 0.11 mmol). The mixture was stirred overnight at room temperature. The reaction was isolated by washing with aqueous NaHCO3 and water to give crude product that was purified on a silica gel column eluting with 5-10% 1 M NH3 in methanol and methylene chloride to give the title compound (739 mg) in a 76% yield.

출처