تفاعل #1015181

معادلة التفاعل

2-chlorosulfonylbenzoyl chloride

Intermediate 121

2-chlorosulfonylbenzoyl chloride

N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)amine

Intermediate 120

N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)amine

tert-butyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate

Intermediate 122

tert-butyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate

→

tert-butyl (1aRS,7bSR)-5-{2-[N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)carbamoyl]-benzenesulfonylamino}-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate

المردود 6.2%

المذيبات

DCM

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated at 30-35° C. overnight
2. 2
   درجة الحرارةAfter cooling
3. 3
   تركيزthe mixture was concentrated under vacuum
4. 4
   أخرىthe residue was purified by HPLC (C18)

الإجراء التجريبي

A solution of N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)amine (Intermediate 120, 0.179 g) in DCM (2 mL) was added dropwise with stirring to a cooled solution of 2-chlorosulfonylbenzoyl chloride (Intermediate 121, 0.17 g) in DCM (20 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour then a solution of tert-butyl (1aRS,7bSR)-5-amino-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (Intermediate 122, 0.185 g) in DCM (2 mL) was added. The resultant mixture was stirred and heated at 30-35° C. overnight. After cooling, the mixture was concentrated under vacuum and the residue was purified by HPLC (C18) to give tert-butyl (1aRS,7bSR)-5-{2-[N-(2,4-dimethoxybenzyl)-N-(3-dimethylaminopropyl)carbamoyl]-benzenesulfonylamino}-1,1a,2,7b-tetrahydro-cyclopropa-[c]chromene-4-carboxylate (0.03 g) as a yellow oil.

المصدر