Method for producing polyalkylene glycol derivative having amino group at end

• US 10,550,136 B2
• Filed: 06/27/2019
• Issued: 02/04/2020
• Est. Priority Date: 12/04/2014
• Status: Active Grant

• Current Assignee: Shin-Etsu Chemical Company Limited
• Original Assignee: Shin-Etsu Chemical Company Limited
• Inventors: Suka, Yuki, Harada, Yuji, Watanabe, Takeru, Nonaka, Shiori
• Primary Examiner(s): Fetterolf, Brandon J
• Assistant Examiner(s): Adzamli, Kofi
• Application Number:
  US16/454,552
• Publication Number:
  US 20190315777A1
• Time in Patent Office: 222 Days
• Field of Search: None
• CPC Class Codes: C07F 7/0892 Compounds with a Si-O-N linkage
• CPC Class Codes: C07F 7/10 containing nitrogen having a Si-N linkage
• CPC Class Codes: C08G 65/12 containing organo-metallic compounds or metal hydrides
• CPC Class Codes: C08G 65/2609 containing aliphatic hydroxyl groups
• CPC Class Codes: C08G 65/33303 containing amino group
• CPC Class Codes: C08G 65/33306 acyclic
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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_A³O(R_A⁴O)_k−1R_A⁴O⁻M⁺  (V)

• • wherein R_A³ represents a linear, branched, or cyclic hydrocarbon group having 1 to 20 carbon atoms; R_A⁴ 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_A² represents a linear, branched, or cyclic hydrocarbon group having 1 to 6 carbon atoms; and X represents a leaving group.

Claims

1. A polyalkylene compound derivative having a protected amino group of formula (II-1):