* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
b) 3-[2-(2-{2-[2-(2-Carboxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]propionic acid (40) A solution of tert-butyl 3-[2-(2-{2-[2-(2-tert-butoxycarbonylethoxy)ethoxy]ethoxy}-ethoxy)ethoxy]propionate 24 in 50 ml of methylene chloride and 50 ml of trifluoro-acetic acid is stirred for 2 h and then concentrated. The residue is taken up in 1N hydrochloric acid and extracted with methylene chloride. The organic phase is concentrated and contains 40. C14H26O9 (338.36) MS (ESI) 339 (M+H)
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 1h;
3-(2-{2-[2-(2-{2-[2-(4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylcarbamoyl)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionic acid Compound from EXAMPLE 20 (0.6 g, 1.8 mmol) was dissolved in dichloromethane (10 ml) and 4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylamine (0.3 g, 1.4 mmol) followed by EDCI (0.28 g, 1.8 mmol) was added at RT. After 1 hr at RT the RM was washed with water and dried over sodium sulfate. Evaporation of volatiles and purification over silica gel column with 1 to 15% methanol in dichloromethane provided title compound as gum (0.47 g, 32%).
32%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 1h;
Compound from Example 20 (0.6 g, 1.8 mmol)was dissolved in dichloromethane (10 ml) and 4-{2-[2-(2-Methyl-[1,3]dioxolan-2-ylmethyl)-[1,3]dioxolan-2-yl]-ethyl}-phenylamine (0.3 g, 1.4 mmol) followed by EDCI (0.28 g, 1.8 mmol) was added at RT. After 1 hr at RT the RM was washed with water and dried over sodium sulfate. Evaporation of volatiles and purification over silica gel column with 1 to 15% methanol in dichloromethane provided title compound as gum (0.47 g, 32%).
With methoxybenzene; trifluoroacetic acid; at 0 - 20℃; for 3h;
A solution of 3-{2-[2-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (6 g, 18.6 mmol) in anisole (20 ml) was cooled in an ice bath and trifluroacetic acid (65 g) was added. After 3 hrs at RT volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and then extracted with ethyl acetate (3×50 ml). Combined organic layers were washed with brine and dried over sodium sulfate. Removal of volatiles under the reduced pressure provided the product as colorless liquid which solidified upon refrigeration (3.8 g, 82%).
82%
A solution of 3-{2-[2-(2-{2-[2-(2-tert-Butoxycarbonyl-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester (6 g, 18.6 mmol) in anisole (20 ml) was cooled in an ice bath and trifluoroacetic acid (65 g) was added. After 3 hrs at RT volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate (50 ml) and 5% sodium bicarbonate solution. The aqueous layer was acidified with 1 N HCl, saturated with NaCl and then extracted with ethyl acetate (3*50 ml). Combined organic layers were washed with brine and dried over sodium sulfate. Removal of volatiles under the reduced pressure provided the product as colorless liquid which solidified upon refrigeration (3.8 g, 82%).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
