Ammonium Chloride → HCID 49854668, Verbindung

HRID 39406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 39406
C[C:2](C(C)CC1C=CC=CC=1)([C@H:6]1[CH2:11][C@@H:10]([CH2:12]S(C2N(C3C=CC=CC=3)N=NN=2)(=O)=O)[O:9][C:8]([CH3:28])([CH3:27])[O:7]1)[C:3]([O-:5])=[O:4].[F:38][C:39]1[CH:44]=[CH:43][C:42]([C:45]2[C:50]([CH:51]=O)=[C:49]([CH:53]([CH3:55])[CH3:54])[N:48]=[C:47]([N:56]([CH3:61])[S:57]([CH3:60])(=[O:59])=[O:58])N=2)=[CH:41][CH:40]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl-].[NH4+:73]>O1CCCC1.C(OCC)(=O)C>[F:38][C:39]1[CH:40]=[CH:41][C:42]([C:45]2[C:50](/[CH:51]=[CH:12]/[C@H:10]3[O:9][C:8]([CH3:27])([CH3:28])[O:7][C@@H:6]([CH2:2][C:3]([O:5][C:50]([CH3:51])([CH3:49])[CH2:45][C:42]4[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=4)=[O:4])[CH2:11]3)=[C:49]([CH:53]([CH3:54])[CH3:55])[N:48]=[C:47]([N:56]([CH3:61])[S:57]([CH3:60])(=[O:58])=[O:59])[N:73]=2)=[CH:43][CH:44]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 10473133N-(4-(4-Fluorophenyl)-5-formyl-6-(1-methylethyl)-2-pyrimidinyl)-N-methylmethanesulfonamideHCID 867620332-methyl-1-phenylpropan-2-yl-2-((4R,6S)-2,2-dimethyl-6-((1-phenyl-1H-tetrazol-5-ylsulfonyl)methyl)-1,3-dioxan-4-yl)acetate

Produkt 1

HCID 49854668HCID 49854668, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-methyl-1-phenylpropan-2-yl-2-((4R,6S)-2,2-dimethyl-6-((1-phenyl-1H-tetrazol-5-ylsulfonyl)methyl)-1,3-dioxan-4-yl)acetate (25.75 g) prepared in Example 15 and N-(4-(4-fluorophenyl)-5-formyl-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide (15.55 g) were dissolved in tetrahydrofuran (60 ml), followed by cooling to −78° C. under an argon atmosphere, and lithium bis(trimethylsilyl)amide (120 ml of a 0.5M solution in tetrahydrofuran) was added thereto over 10 minutes, followed by stirring at the same temperature for 2 hours. Then, the mixture was stirred for 4 hours while warming to 0° C. A saturated ammonium chloride aqueous solution (250 ml) was added to the reaction liquid, followed by stirring for 10 minutes, and ethyl acetate (500 ml) was added thereto. The organic layer was separated and washed successively with purified water (250 ml), a saturated sodium bicarbonate aqueous solution (250 ml,) and a saturated sodium chloride aqueous solution (250 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting solid was stirred with isopropyl ether, filtered and collected. This solid was dried in a vacuum oven overnight (50° C., 200 mbar) to give the title compound (26.06 g, 90%).

Aufarbeitung

  1. stirringThen, the mixture was stirred for 4 hours
  2. temperaturewhile warming to 0° C
  3. stirringby stirring for 10 minutes
  4. customThe organic layer was separated
  5. washwashed successively with purified water (250 ml)
  6. dry with materiala saturated sodium bicarbonate aqueous solution (250 ml,) and a saturated sodium chloride aqueous solution (250 ml), dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. stirringThe resulting solid was stirred with isopropyl ether
  10. filtrationfiltered
  11. customcollected
  12. customThis solid was dried in a vacuum oven overnight (50° C., 200 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-55208ee373da48e39599c46f7212f1b8
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524914B2

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