3-(Trifluoromethyl)phenol → HCID 21921562, Verbindung

HRID 1245097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245097
FC1C=C[C:5]([C:6]([OH:8])=[O:7])=CC=1[N+]([O-])=O.F[C:15](F)(F)[C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].CC(C)[N:50]=C=NC(C)C.[CH:57]1[CH:58]=[CH:59][C:60]2N(O)N=N[C:61]=2[CH:62]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[N+:25]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][C:36]=1[O:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:45])([F:46])[F:47])[CH:39]=1)[C:31]([OH:33])=[O:32])([O-:27])=[O:26].[C:19]1([C:62]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH:18]=[CH:17][C:16]([CH2:15][C@H:5]([NH:50][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][C:36]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=3)=[C:28]([N+:25]([O-:27])=[O:26])[CH:29]=2)[C:6]([OH:8])=[O:7])=[CH:21][CH:20]=1

Komponenten

9

Edukt 5

HCID 73763-(Trifluoromethyl)phenolHCID 12734DiisopropylcarbodiimideHCID 679874-Fluoro-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 21921562HCID 21921562, Verbindung

Produkt 2

HCID 21921562HCID 21921562, VerbindungAusbeute 81 %HCID 58717697HCID 58717697, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3-Nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (530 mg, 81%) was prepared from 4-fluoro-3-nitro-benzoic acid (370 mg, 2.0 mmol) and 3-trifluoromethyl phenol (324 mg, 2.0 mmol) as in general procedure B. To Wang resin (60 mg, 0.06 mmol, 1.1 mmol/g) loaded with 4-L-biphenylalanine were added 82 mg of (0.25 mmol) 3-nitro-4-(3-trifluoromethyl-phenoxy)-benzoic acid (82 mg, 0.25 mmol), 1.0 M DIC (1.5 mL, 1.5 mmol) in DMF, 1.0 M HOBt (1.5 mL, 1.5 mmol) in DMF, and a catalytic amount of DMAP. The resulting mixture was left on shaker overnight. The resin was washed with DMF, MeOH, DCM three times of each and cleaved with 20% TFA in DCM. The residue obtained after removing the solvent was purified by chromatography to give the title compound (26 mg, 79%).

Aufarbeitung

  1. washThe resin was washed with DMF, MeOH, DCM three times of each and
  2. customThe residue obtained
  3. customafter removing the solvent
  4. customwas purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-db2cf75198264026bf372f0770fc85e4
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122580B2

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