2-Dimethylaminopyridine → 2',3'-difluoro-4'-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethyl-heptyloxycarbonyl]-phenyl ester

HRID 48124

Reaktionsgleichung

Reaktionsgleichung von HRID 48124
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH:5]=[CH:4][C:3]=1[C:27]1[CH:32]=[CH:31][C:30]([C:33]([OH:35])=[O:34])=[CH:29][CH:28]=1.[F:36][C:37]([F:56])([F:55])[C@H:38]([O:45][C:46](=[O:54])[C:47]1[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=1)[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44].CN(C1C=CC=CN=1)C>C1COCC1.C(N=C=NC(C)C)(C)C>[F:36][C:37]([F:55])([F:56])[C@H:38]([O:45][C:46]([C:47]1[CH:48]=[CH:49][C:50]([O:34][C:33]([C:30]2[CH:31]=[CH:32][C:27]([C:3]3[CH:4]=[CH:5][C:6]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:20])([F:18])[F:19])=[C:7]([F:8])[C:2]=3[F:1])=[CH:28][CH:29]=2)=[O:35])=[CH:51][CH:52]=1)=[O:54])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]

Komponenten

6

Edukt 3

HCID 218852-DimethylaminopyridineHCID 145492174-hydroxybenzoic acid (R)-1-trifluoromethyl-heptyl esterHCID 220162542',3'-Difluoro-4'-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid

Produkt 1

HCID 867593732',3'-difluoro-4'-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethyl-heptyloxycarbonyl]-phenyl esterAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 12734DiisopropylcarbodiimideLösungsmittel

Versuchsvorschrift

To a solution of 2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid (14 A) (1 equi.), (4-hydroxy benzoic acid (R)-1-trifluoromethyl-heptyl ester (7) (1 equi.), and DMAP (dimethylaminopyridine) (0.1 equi.) in THF (25 mL/mmole), DIC (diisopropyl carbodiimide) (1.2 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h, quenched with water, extracted with ethyl acetate:hexane(1:1), washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) gave 2′,3′-difluoro-4′-(5,5,6,6,7,7,8,8,8-nonafluoro-octyloxy)-biphenyl-4-carboxylic acid 4-[(R)-1-trifluoromethyl-heptyloxycarbonyl]-phenyl ester (15A) as a white solid (65%).

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with ethyl acetate:hexane(1:1)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (5% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7244747d2dfe4650a008e9fa1afb83a6
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703082B1

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