Trifluoroacetic acid → 4-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acid

HRID 2266864

Reaktionsgleichung

Reaktionsgleichung von HRID 2266864
C[O:2][C:3]([C:5]1[O:6][C:7]([CH3:29])=[C:8]([CH2:10][N:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]([F:28])[F:27])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH3:12])[CH:9]=1)=[O:4].FC(F)(F)C(O)=O>O1CCCC1>[F:28][CH:26]([F:27])[O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:15]=[CH:14][C:13]([N:11]([CH2:10][C:8]3[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[O:6][C:7]=3[CH3:29])[CH3:12])=[CH:18][CH:17]=2)=[CH:24][CH:23]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 588241664-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acid methyl ester

Produkt 1

HCID 184445654-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acidAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-{[(4′-difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl}-5-methyl-furan-2-carboxylic acid methyl ester (175) (30 mg, 0.07 mmoles) in dry tetrahydrofuran (20 ml) was treated with potassium trimethylsilanoate (19 mg, 0.15 mmoles) and the mixture stirred under an argon atmosphere for 30 hours. Trifluoroacetic acid was added until the pH=2. After evaporation of the solvent, the residue was purified by HPLC to afford compound 176 (4.8 mg) as a white solid. LC/MS System D; Rt=9.42 mins, m/z (ES+)=388 (M+H for C21H19F2NO4).

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ebcf62f07b9441b182149f0d8233c6c4
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858644B2

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