2-(2-(2-Aminoethoxy)ethoxy)acetic acid

White to off-white crystalline powder

In a 3000L three-necked flask equipped with mechanical stirring, condenser and constant pressure dropping funnel, 330 g of crude product (Intermediate 3) was dissolved in 1000 ml of ethanol, and 350 g of 30% NaOH solution was added dropwise.After the completion of the dropwise addition, the mixture was heated to reflux, and monitored by TLC, the intermediate 3 was completely disappeared, and the temperature was lowered. The pH was adjusted to 9 with hydrochloric acid, and a solution of 337 g of Fmoc-Osu in 1000 ml of ethanol was added dropwise.If the pH has dropped, add sodium bicarbonate and keep it at around 8.TLC was monitored until Intermediate 4 disappeared. The pH was adjusted to 1-2 with hydrochloric acid, the ethanol was distilled off, 1000 ml of water was added, and the mixture was extracted three times with ethyl acetate 500*3, and washed twice with saturated brine.The ethyl acetate was concentrated to give 285 g of crude material.Recrystallization from 1000 ml of ethyl acetate gave 200 g of product[2-[1-(Fmoc-Amino)ethoxy]ethoxy]acetic acid, yield 51.9%.In a 3000L three-necked flask equipped with mechanical stirring, condenser and constant pressure dropping funnel, 330 g of crude product was dissolved in 1000 ml of ethanol, and 350 g of 30% NaOH solution was added dropwise.After the completion of the dropwise addition, the mixture was heated to reflux, and monitored by TLC until the etherification intermediate completely disappeared and the temperature was lowered.The pH was adjusted to 9 with hydrochloric acid, and a solution of 337 g of Fmoc-Osu in 1000 ml of ethanol was added dropwise, and if the pH was decreased, Add sodium bicarbonate and keep at around 8.TLC was monitored until the free amino intermediate disappeared. Adjust the pH to 1-2 with hydrochloric acid, The ethanol was distilled off, 1000 ml of water was added, and the mixture was extracted three times with ethyl acetate 500*3, and washed twice with saturated brine.Concentrate ethyl acetate to give 280 g of crude product.Recrystallization from 1000 ml of ethyl acetate gave 198 g of the product [2-[1-(Fmoc-amino)ethoxy]ethoxy]acetic acid in a yield of 51.38%.In a 3000L three-necked flask equipped with mechanical stirring, condenser and constant pressure dropping funnel, 330 g of crude product (Intermediate 3) was dissolved in 1000 ml of ethanol, and 350 g of 30% NaOH solution was added dropwise.After the completion of the dropwise addition, the mixture was heated to reflux, and monitored by TLC, the intermediate 3 was completely disappeared, and the temperature was lowered. The pH was adjusted to 9 with hydrochloric acid, and a solution of 337 g of Fmoc-Osu in 1000 ml of ethanol was added dropwise.If the pH has dropped, add sodium bicarbonate and keep it at around 8.TLC was monitored until Intermediate 4 disappeared. The pH was adjusted to 1-2 with hydrochloric acid, the ethanol was distilled off, 1000 ml of water was added, and the mixture was extracted three times with ethyl acetate 500*3, and washed twice with saturated brine.The ethyl acetate was concentrated to give 285 g of crude material.Recrystallization from 1000 ml of ethyl acetate gave 200 g of product[2-[1-(Fmoc-Amino)ethoxy]ethoxy]acetic acid, yield 51.9%.In a 3000L three-necked flask equipped with mechanical stirring, condenser and constant pressure dropping funnel, 330 g of crude product was dissolved in 1000 ml of ethanol, and 400 g of 30% NaOH solution was added dropwise.After the addition is completed, the mixture is heated to reflux, and the TLC is monitored. The etherification intermediate disappears completely and the temperature is lowered.The pH was adjusted to 9 with hydrochloric acid, and 259 g of Fmoc-Cl was added dropwise to dissolve in 1000 ml of ethanol solution.If the pH has dropped, add sodium bicarbonate and keep it at around 8.TLC was monitored until the free amino intermediate disappeared. Adjust the pH to 1-2 with hydrochloric acid, Distill the ethanol, add 1000 ml of water, and extract three times with ethyl acetate 500*3.Wash twice with saturated brine and concentrate ethyl acetate to give 288 g of crude material.Recrystallization from 1000 ml of ethyl acetate gave 203 g of product[2-[1-(Fmoc-Amino)ethoxy]ethoxy]acetic acid, yield 52.68%.

Molecular Weight:163.17
XLogP3:-3.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:163.08445790
Monoisotopic Mass:163.08445790
Topological Polar Surface Area:81.8
Heavy Atom Count:11
Complexity:107
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes