Phosphate → HCID 178460582, Verbindung

HRID 1766947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1766947
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:38])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C@H:10]([S:12][C@@H:13]1[CH2:18][O:17][C@@H:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[F:31])[O:15][CH2:14]1)[CH3:11].[H-].[Na+].[CH2:41]([O:44][P:45]([O:51][CH2:52][C:53]1[CH:57]=[CH:56][S:55][C:54]=1[C:58](Cl)=[O:59])([O:47][CH2:48][CH:49]=[CH2:50])=[O:46])[CH:42]=[CH2:43].P([O-])([O-])([O-])=O>COCCOC>[CH2:48]([O:47][P:45]([O:51][CH2:52][C:53]1[CH:57]=[CH:56][S:55][C:54]=1[C:58]([O:38][C@:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])([CH2:32][N:33]1[CH:37]=[N:36][CH:35]=[N:34]1)[C@H:10]([S:12][C@@H:13]1[CH2:18][O:17][C@@H:16](/[CH:19]=[CH:20]/[CH:21]=[CH:22]/[C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][C:24]=2[F:31])[O:15][CH2:14]1)[CH3:11])=[O:59])([O:44][CH2:41][CH:42]=[CH2:43])=[O:46])[CH:49]=[CH2:50]

Komponenten

6

Edukt 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 21110456HCID 21110456, VerbindungHCID 178462432HCID 178462432, Verbindung

Produkt 1

HCID 178460582HCID 178460582, VerbindungAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 4-[(1E,3E)-4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-1,3-butadienyl]-3-fluorobenzonitrile (699.1 mg, 1.29 mmol) described in Reference example 1 in 1,2-dimethoxyethane (10 ml) was cooled to 0° C., and sodium hydride (55% dispersion in mineral oil; 67.5 mg, 1.55 mmol) was added thereto, and the resulting mixture was stirred at room temperature for 3 hours. To the mixture was added a solution of the crude 3-[[bis(allyloxy)phosphoryl]oxymethyl]-2-thenoyl chloride obtained above in 1,2-dimethoxyethane (2 ml), and the mixture was stirred at room temperature for 20 minutes and cooled to 0° C., then a phosphate buffer solution (pH 7) was added to the reaction mixture to stop the reaction, and the product was extracted with ethyl acetate. The crude product was subjected to chromatography on a silica gel (40 g) column (eluent; ethyl acetate:hexane=3:2˜5:1) to give the title compound (520.6 mg, 48% yield) as a pale yellow amorphous solid.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 20 minutes
  2. temperaturecooled to 0° C.
  3. customthe reaction
  4. extractionthe product was extracted with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5400db58f08a4ddf934055db56af7270
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07230023B2

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