| Identification | Back Directory | [Name]
[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)- | [CAS]
158938-08-0 | [Synonyms]
Anidulafungin Impurity 3
Side chain of Anidulafungin
4-(4'-Pentoxy-4-biphenylyl)benzoic acid
4-{4-[4-(Pentyloxy)phenyl]phenyl}benzoic acid
4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)-
4-(4''-pentyloxy-1,1':4',1''-terphenyl)-carboxylic acid
4''-(pentyloxy)-[1,1':4',1''-Terphenyl]-4-carboxylic acid
[1,1':4',1''-Terphenyl]-4-carboxylic acid, 4''-(pentyloxy)- | [EINECS(EC#)]
691-410-4 | [Molecular Formula]
C24H24O3 | [MDL Number]
MFCD17019206 | [MOL File]
158938-08-0.mol | [Molecular Weight]
360.45 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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