Molecular gelators and uses thereof

Patent metadata

Field	Value
Publication number	US-10851273-B2
Application number	US-201615778923-A
Country	US
Kind code	B2
Filing date	Nov 29, 2016
Priority date	Feb 12, 2016
Publication date	Dec 1, 2020
Grant date	Dec 1, 2020

Abstract

In accordance with the present subject matter there is provided a compound of Formula I wherein, R 1 is substituted C 1 to C 10 alkyl; and R 2 is substituted C 1 to C 10 alkyl, a process for preparing a compound of Formula I, and a gel comprising a compound of Formula I. There is also provided a process for separating a hydrophobic material from a mixture of hydrophobic and hydrophilic material using a compound of Formula I.

First claim

We claim:

1. A compound having the Formula:

wherein,
R 1 is substituted C 1 to C 10 alkyl;
R 2 is substituted C 1 to C 10 alkyl.

2. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 5 alkyl substituted with C 1 to C 3 alkyl, C 5 -C 10 aryl, C 6 -C 10 heteroaryl, or a heteroatom selected from the group consisting of O, N, and S, wherein the heteroatom is further substituted with C 1 to C 3 alkyl, C 5 -C 10 aryl, or C 6 -C 10 heteroaryl.

3. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 3 alkyl substituted with C 1 to C 2 alkyl, C 5 -C 8 aryl, C 6 -C 10 heteroaryl, or a heteroatom selected from the group consisting of O, N, and S, wherein the heteroatom is further substituted with C 1 to C 2 alkyl, C 5 -C 10 aryl, or C 6 -C 10 heteroaryl.

4. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 3 alkyl substituted with C 1 to C 2 alkyl, C 5 -C 8 aryl, C 6 -C 10 heteroaryl, or a heteroatom selected from the group consisting of O, N, and S, wherein the heteroatom is further substituted with C 1 to C 2 alkyl.

5. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 3 alkyl substituted with C 1 to C 2 alkyl, C 5 -C 8 aryl, C 6 -C 10 heteroaryl, or S further substituted with C 1 to C 2 alkyl, wherein both R 1 and R 2 are not C 1 to C 3 alkyl substituted with S further substituted with C 1 to C 2 alkyl.

6. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 2 alkyl substituted with C 1 , C 6 aryl, C 8 heteroaryl with N as the heteroatom, or S further substituted with C 1 alkyl, wherein both R 1 and R 2 are not C 1 to C 2 alkyl substituted with S further substituted with C 1 alkyl.

7. The compound as claimed in claim 1 , wherein R 1 and R 2 are independently selected from C 1 to C 3 alkyl substituted with C 1 to C 2 alkyl, or S further substituted with C 1 to C 2 alkyl, wherein both R 1 and R 2 are not C 1 to C 3 alkyl substituted with S substituted with C 1 to C 2 alkyl.

8. The compound as claimed in claim 1 , wherein R 1 is C 1 to C 3 alkyl substituted with C 1 to C 2 alkyl, and R 2 is C 1 to C 3 alkyl substituted with S further substituted with C 1 to C 2 alkyl.

9. The compound as claimed in claim 1 , wherein R 1 is C 2 alkyl substituted with C 1 alkyl, and R 2 is C 2 alkyl substituted with S further substituted with C 1 alkyl.

10. A process for preparing the compound of claim 1 , comprising
(a) coupling the methyl ester of an amino acid with palmitic acid chloride in dry chloroform in presence of triethylamine;
(b) purifing the ester-protected long-chain amide or monopeptide;
(c) hydrolyzing the product using NaOH in MeOH followed by acidification using HCI to produce a monopeptide carboxylic acid;
(e) coupling the monopeptide carboxylic acid with another methyl ester protected amino acid using DCC in dry dichloromethane (DCM) in presence of HOBT and DMAP;
(f) hydrolysis the product using NaOH in MeOH followed by acidification using HCI.

Assignees

• Hindustan Petroleum Corp Ltd

Inventors

• Ravishankar Raman
• Chinthalapati Siva Kesava Raju
• Pramanik Bhaskar
• Kar Tanmoy
• Chalapathi Rao Peddi Venkat
• Nettem Venkateswarlu Choudary

Classifications

• C07K5/06017

  and aliphatic · CPC title

• C07K5/06052

  Val-amino acid · CPC title

• C07K5/06165

  and Pro-amino acid; Derivatives thereof · CPC title

• C07K5/0606

  the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr · CPC title

• C07K5/06078

  and aromatic or cycloaliphatic · CPC title