[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)- Chemical Properties

Boiling point:

557.9±43.0 °C(Predicted)

Density 

1.117

storage temp. 

Sealed in dry,Room Temperature

pka

4.23±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C24H24O3/c1-2-3-4-17-27-23-15-13-21(14-16-23)19-7-5-18(6-8-19)20-9-11-22(12-10-20)24(25)26/h5-16H,2-4,17H2,1H3,(H,25,26)

InChIKey

APIUMVXKBCYBSC-UHFFFAOYSA-N

SMILES

C1(C2=CC=C(C3=CC=C(OCCCCC)C=C3)C=C2)=CC=C(C(O)=O)C=C1

[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)- Usage And Synthesis

Chemical Properties

off-white solid

Uses

4''''-(Pentyloxy)-[1,1'':4'',1''''-terphenyl]-4-carboxylic Acid is an intermediate used in the synthesis of Anidulafungin (A673000) which is a semisynthetic echinocandin that inhibits glucan synthase, an enzyme important in the formation of (1→3)-β-D-glucan, a major fungal cell wall component, and thus is used as antifungal drug.

Synthesis

General procedure for the synthesis of 4''-n-pentyloxy[1,1':4',1'']terphenyl-4-carboxylic acid from the compound (CAS: 289706-68-9) and 4'-iodo-[1,1'-biphenyl]-4-carboxylic acid: 20.1 g of 4'-iodo[1,1']biphenyl-4-carboxylic acid, 13.1 g of sodium carbonate and 21.4 g of 4-n-pentyloxyphenylboronic acid glycol ester were added to 260 g of dimethyl sulfoxide (DMSO). Subsequently, 160 mg of PdCl2(PPh3)2 was added as a catalyst and the reaction mixture was heated to 100-110 °C and maintained for 2 hours. Upon completion of the reaction, the mixture was cooled to 40 °C and filtered, and the solid was washed with DMSO. The resulting solid was suspended in 100 mL of water, heated to 80 °C and 47 g of 37% sulfuric acid was slowly added dropwise over a period of 1 hour. After the dropwise addition, the reaction solution was continued to be stirred at 80 °C for 30 min, followed by cooling to 40 °C and filtration. Finally, the solid was dried and crystallized from dimethylacetamide to afford 18 g (81% yield) of 4''-n-pentyloxy[1,1':4',1'']terphenyl-4-carboxylic acid of >99% purity.

References

[1] Patent: EP1156997, 2004, B1. Location in patent: Page 11
[2] Patent: EP1156997, 2004, B1. Location in patent: Page 11
[3] Patent: EP1156997, 2004, B1. Location in patent: Page 11
[4] Patent: EP1156997, 2004, B1. Location in patent: Page 10
[5] Patent: EP1156997, 2004, B1. Location in patent: Page 10; 11

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