تفاعل #164245

معادلة التفاعل

(5-methyl-thiophen-2-yl)-phenylamino-acetic acid hydrochloride

(R)-quinuclidin-3-ol

1H-benzo[d][1,2,3]triazol-1-ol

DCC

DCC

→

title compound

المردود 63.8%

(5-methyl-thiophen-2-yl)-phenylamino-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester

المردود 63.8%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction is shaken at RT for other 3 hours
2. 2
   ترشيحThe resin is filtered off
3. 3
   غسيلwashed several time with EtOAc
4. 4
   تركيزThe solvent is concentrated
5. 5
   غسيلwashed with aq. NaHCO3, water and brine
6. 6
   تجفيفThe organic phase is dried over Na2SO4
7. 7
   أخرىevaporated

الإجراء التجريبي

To a solution of (5-methyl-thiophen-2-yl)-phenylamino-acetic acid hydrochloride (I268) (220 mg, 0.77 mmol), (R)-quinuclidin-3-ol (338 mg, 2.66 mmol) and 1H-benzo[d][1,2,3]triazol-1-ol (180 mg, 1.33 mmol) in dry THF (15 mL), is added PS-DCC (1.0 g, 1.330 mmol) and the mixture is shaken at RT for 15 hours. Then (R)-quinuclidin-3-01 (49.3 mg, 0.39 mmol) and PS-DCC (291 mg, 0.39 mmol) are added again and the reaction is shaken at RT for other 3 hours. The resin is filtered off and washed several time with EtOAc. The solvent is concentrated and washed with aq. NaHCO3, water and brine. The organic phase is dried over Na2SO4 and evaporated to obtain the title compound as a brown oil (175 mg, 63% yield).

المصدر