Hydrochloric Acid → HCID 135446415, Verbindung

HRID 1672706Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672706
[O:1]=[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([CH2:42][C:43]3[CH:52]=[CH:51][C:46]([C:47]([O:49]C)=[O:48])=[CH:45][CH:44]=3)[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)=[CH:28][CH:27]=3)=[CH:9][CH:8]=2)[NH:3]1.[OH-].[Li+].Cl>C1COCC1.O>[O:1]=[C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][N:15]([CH2:42][C:43]3[CH:44]=[CH:45][C:46]([C:47]([OH:49])=[O:48])=[CH:51][CH:52]=3)[CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]4[CH:37]=[CH:36][C:35]([C:38]([F:41])([F:40])[F:39])=[CH:34][CH:33]=4)=[CH:28][CH:27]=3)=[CH:11][CH:12]=2)[NH:3]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 135978829HCID 135978829, Verbindung

Produkt 1

HCID 135446415HCID 135446415, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 32.7 mg (0.05 mmol) of methyl 4-[({2-[4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)phenyl]ethyl}-{2-[2-(4′-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]ethyl}amino)methyl]-benzoate from Example 11A in 2 ml of THF and 2 ml of water is mixed with 2.2 mg (0.09 mmol) of lithium hydroxide and stirred at 50° C. for 12 h. After cooling, the THF is stripped off and the aqueous phase is adjusted to pH 4-5 with 1 M hydrochloric acid. It is then extracted three times with ethyl acetate, and the combined organic phases are dried over sodium sulfate. The residue obtained after filtration and concentration is purified by preparative HPLC. 7.4 mg (0.01 mmol, 23% yield) of a colorless oil are obtained.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionIt is then extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. customThe residue obtained
  5. filtrationafter filtration and concentration
  6. customis purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-97b6d5b81e1e40f49d19b117d2e11584
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998988B2

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