HCID 178447445, Verbindung → HCID 178464334, Verbindung

HRID 1036527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1036527
[N+:1]([C:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:23]3)[CH:17]=2)[CH:12]=1)([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][C@H:22]3[CH2:27][CH2:26][C@H:25]([C:28]([F:29])([F:30])[F:31])[CH2:24][CH2:23]3)[CH:17]=2)[CH:12]=1)([CH3:10])[CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Komponenten

4

Edukt 1

HCID 178447445HCID 178447445, Verbindung

Produkt 1

HCID 178464334HCID 178464334, VerbindungAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

To a solution of 4-nitro-4-[6-(trans-4-trifluoromethyl-cyclohexyloxy)-naphthalen-2-yl]-pentanoic acid (0.099 g, 0.22 mmol) in acetic acid (2.00 mL, Fisher) at 20° C. was added zinc (0.185 g, 2.83 mmol, Aldrich). The mixture was stirred for 45 minutes at room temperature. The mixture was heated at 50° C. and stirred. After 2.5 h, the mixture was diluted in acetic acid, filtered and concentrated to dryness under reduced pressure. Purification was by preparative HPLC. The fractions were dried to give 61 mg (52%) product as TFA salt. MS: m/z=432.10 [M+Na]+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 7.62-7.74 (m, 3H), 7.36 (dd, J=8.8, 1.8 Hz, 1H), 7.03-7.12 (m, 2H), 4.21-4.32 (m, 1H), 2.20-2.41 (m, 4H), 1.91-2.19 (m, 5H), 1.72 (s, 3H), 1.35-1.51 (m, 4H).

Aufarbeitung

  1. temperatureThe mixture was heated at 50° C.
  2. stirringstirred
  3. waitAfter 2.5 h
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification
  7. customThe fractions were dried

Quellen und Nachweise

ORD-Eintrag
ord-2ff9bf3ff857425a87fb7ba340404cc8
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

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