Method for producing polyalkylene glycol derivative having amino group at end

Patent metadata

Field	Value
Publication number	US-11066430-B2
Application number	US-201916454785-A
Country	US
Kind code	B2
Filing date	Jun 27, 2019
Priority date	Dec 4, 2014
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

A method simply produces a narrowly distributed and high-purity polyalkylene glycol derivative having an amino group at an end without using a heavy metal catalyst. A method for producing a polyalkylene glycol derivative having an amino group at the end by reacting a compound represented by the general formula (V) with an alkylene oxide, then reacting a reaction product with an electrophile represented by the general formula (I), and deprotecting the obtained product without using a heavy metal:

R A 3 O(R A 4 O) k−1 R A 4 O − M +   (V)
wherein R A 3 represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R A 4 represents an alkylene group having 2 to 8 carbon atoms; k represents an integer of 2 to 5; and M represents an alkali metal;

wherein R A 1a and R A 1b each independently represent a protective group of the amino group, or one of R A 1a and R A 1b represents H and the other represents a protective group of the amino group, or R A 1a and R A 1b bind to each other to form a cyclic protective group, and the protective group is deprotectable without using a heavy metal; R A 2 represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

First claim

What is claimed is:

1. An alcohol compound having silyl-protected amino group of formula (I-2-A):

wherein R 1 are each independently a linear monovalent hydrocarbon group having 1 to 6 carbon atoms, or a branched or cyclic monovalent hydrocarbon group having 3 to 6 carbon atoms; and
R A 2 is a saturated linear divalent hydrocarbon group having 3 to 6 carbon atoms, or a branched or cyclic divalent hydrocarbon group having 3 to 6 carbon atoms.

2. A method for producing the alcohol compound having silyl-protected amino group of formula (I-2-A) according to claim 1 , comprising:
protecting an amino group of an aminoalkyl compound of formula (I-0-A) with two trialkylsilyl groups of Si(R 1 ) 3, and protecting a hydroxyl group of the compound of formula (I-0-A) with a trialkylsilyl group of Si(R 1 ) 3 to obtain a trisilyl compound of formula (I-1-A):
HO—R A 2 —NH 2   (I-0-A)

wherein R A 2 is the same as R A 2 in formula (I-2-A);

wherein R 1 and R A 2 are the same as R 1 and R A 2 in formula (I-2-A); and
removing only the trialkylsilyl group which protects the hydroxyl group from the compound of formula (I-1-A).

3. The method according to claim 2 , wherein the group of Si(R 1 ) 3 is independently selected from a trimethylsilyl group, a triethylsilyl group, and a tert-butyldimethylsilyl group.

Assignees

• Shinetsu Chemical Co

Inventors

• Suka Yuki
• Harada Yuji
• Watanabe Takeru
• Nonaka Shiori

Classifications

• C08G65/12 Primary

  containing organo-metallic compounds or metal hydrides · CPC title

• Y02P20/55

  Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups · CPC title

• C08G65/33306

  acyclic · CPC title

• C08G65/33303

  containing amino group · CPC title

• C07F7/10

  containing nitrogen {having a Si-N linkage} · CPC title