Water → {(1S,2S,4R)-4-(2,2-Dimethylpropylcarbamoyl)-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-ylmethyl]-2-hydroxyheptyl}carbamic acid t-butyl ester

HRID 1695015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695015
OC1C=CC=CN=1.[C:8]([O:12][C:13](=[O:42])[NH:14][C@H:15]([C@@H:33]1[CH2:37][C@@H:36]([CH2:38][CH2:39][CH3:40])[C:35](=[O:41])[O:34]1)[CH2:16][N:17]1[CH2:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH2:19][C:18]1([CH3:32])[CH3:31])([CH3:11])([CH3:10])[CH3:9].O.[CH3:44][C:45]([CH3:49])([CH3:48])[CH2:46][NH2:47]>>[C:8]([O:12][C:13](=[O:42])[NH:14][C@@H:15]([CH2:16][N:17]1[CH2:22][C:21](=[O:23])[N:20]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH2:19][C:18]1([CH3:32])[CH3:31])[C@@H:33]([OH:34])[CH2:37][C@H:36]([C:35](=[O:41])[NH:47][CH2:46][C:45]([CH3:49])([CH3:48])[CH3:44])[CH2:38][CH2:39][CH3:40])([CH3:11])([CH3:9])[CH3:10]

Komponenten

5

Edukt 4

HCID 962WaterHCID 79882NeopentylamineHCID 66645802{(S)-2-[4-(2-Chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl esterHCID 178516071HCID 178516071, Verbindung

Produkt 1

HCID 66645863{(1S,2S,4R)-4-(2,2-Dimethylpropylcarbamoyl)-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-ylmethyl]-2-hydroxyheptyl}carbamic acid t-butyl esterAusbeute 94 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3.8 mg of 2-hydroxypyridine (0.04 mmol) was added to a solution of 101 mg of {(S)-2-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-yl]-1-[(2S,4R)-5-oxo-4-propyltetrahydrofuran-2-yl]ethyl}carbamic acid t-butyl ester obtained in Example (116i) (0.2 mmol) in (2,2-dimethylpropyl)amine (1 ml), and the mixture was stirred at 80° C. for five hours. The reaction mixture was cooled and then water was added, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=30/1-20/1) to obtain 111 mg of the title compound (yield: 94%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (elution solvent:methylene chloride/methanol=30/1-20/1)

Quellen und Nachweise

ORD-Eintrag
ord-72d5480e901345bc9b3a9dee4209fdc0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158790B2

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