Process for preparing biphenyl compounds

Patent metadata

Field	Value
Publication number	US-10155969-B2
Application number	US-201515516318-A
Country	US
Kind code	B2
Filing date	Oct 5, 2015
Priority date	Oct 3, 2014
Publication date	Dec 18, 2018
Grant date	Dec 18, 2018

Abstract

The present invention relates to a process for preparing a compound having the formula (I), said process comprising the following steps: a) the addition of an oxygen source into a solution of a compound of formula (II), in a water-miscible solvent, b) the addition of a laccase in the solution obtained after step a); and c) the possible recovering of the compound of formula (I) thus obtained.

First claim

The invention claimed is:

1. A process for preparing a compound having the formula (2):

said process comprising:
a) the addition of an oxygen source into a solution of a compound of formula (II-1) in a water-miscible solvent, said compound of formula (II-1) having the following formula:

wherein R is —CN and R 2 is methyl;

b) the addition of a laccase into said solution; and
c) recovering the compound of formula (2).

2. The process of claim 1 , wherein the water-miscible solvent is acetone.

3. The process of claim 1 , wherein the laccase is from Trametes versicolor.

4. The process of claim 1 , wherein the amount of laccase for one gram of compound of formula (II-1), is from 1.5 mg to 75 mg.

5. The process of claim 1 , wherein the solution of the compound of formula (II-1) in a water-miscible solvent is prepared by adding said compound of formula (II-1) in said water-miscible solvent, and adding a buffer solution.

6. The process according to claim 5 , wherein the amount of water-miscible solvent is comprised between 5% and 10% of volume in comparison with the total volume of the mixture formed by said solvent and the buffer solution.

7. The process of claim 1 , wherein the addition of an oxygen source is carried out for a sufficient time to saturate the solution in dissolved oxygen.

8. The process of claim 1 , wherein the solution of the compound of formula (II-1) in the water-miscible solvent is saturated in oxygen.

9. The process of claim 1 , wherein the pH of the solution of the compound of formula (II-1) in the water-miscible solvent is comprised between 4 and 7.

10. A process for the preparation of a compound having the following formula (14):

said process comprising:
a) reacting a compound of formula (V), said compound having the following formula:

wherein R 2 is OMe and R 6 is methyl;
with an alcohol formula R 7 OH, wherein R 7 is a (CH2) 9 —CH═CH2, in the presence of a catalyst and N,N′-diisopropyl carbodiimide; and
b) recovering the compound of formula (14).

11. A process for the preparation of a compound having the following formula (15):

said process comprising:
alkylating the compound of formula (I-1), said compound having the following formula:

wherein R is CHO and R 2 is methyl with a compound R 8 X, X being a halogen, to obtain a compound having the following formula (III-1):

wherein R 2 is methyl and R 8 is methyl,
reacting the compound of formula (III-1) with a Wittig reagent, in order to obtain a compound having the formula (15),
and recovering the compound of formula (15).

12. A process for the preparation of a compound having the following formula (19):

said process comprising:
reacting the compound of formula (I-1), said compound having the following formula:

wherein R is methyl and R 2 is methyl, with a compound R 9 X, wherein R 9 is CH2-CH═CH2 and X is a halogen, in the presence of K 2 CO 3 in a solvent; and
recovering the compound of formula (19).

13. A compound having one of the following formulae:

Assignees

• Univ Bordeaux
• Inst Polytechnique Bordeaux
• Centre Nat Rech Scient
• Univ Bordeaux
• Inst Polytechnique Bordeaux

Inventors

• Grelier Stéphane
• Cramail Henri
• Llevot Audrey
• Carlotti Stéphane
• Grau Etienne

Classifications

• C07C45/71

  being hydroxy groups · CPC title

• C12P7/24

  containing a carbonyl group · CPC title

• C12P13/002 Primary

  Nitriles (-CN) · CPC title

• C07C67/343

  by increase in the number of carbon atoms · CPC title

• C12P7/66

  containing the quinoid structure · CPC title