1-(Benzyloxy)-4-(bromomethyl)benzene → HCID 117778092, Verbindung

HRID 591331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591331
[C:1]([NH:20][C@H:21]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:42][CH:41]=1>O1CCCC1>[CH2:47]([O:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][CH:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:22][C@@H:21]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[NH:20][C:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:45][CH:44]=1)[C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1

Komponenten

4

Edukt 2

HCID 104927561-(Benzyloxy)-4-(bromomethyl)benzeneHCID 14258586di-tert-butyl N-trityl-L-glutamate

Produkt 1

HCID 117778092HCID 117778092, VerbindungAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Di-tert-butyl N-trityl-L-glutamate (1.63 g, 3.25 mmol) was dissolved in tetrahydrofuran (12 ml) and the solution was cooled to −78° C. To the solution was added lithium 1,1,1,3,3,3-hexamethyldisilazide (1M in tetrahydrofuran, 7.14 ml) and, after stirring at −78° C. for 20 min, benzyl 4-(bromomethyl)phenyl ether (1.08 g, 3.90 mmol) in tetrahydrofuran (8 ml) was slowly added. The cooling bath was removed and the reaction mixture was stirred for 2 h. Then, 50 ml of 2 M aqueous hydrogen chloride solution were added and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated under reduced pressure; the residue was purified by silica gel column chromatography to yield 813 mg (30%) of the product.

Aufarbeitung

  1. customThe cooling bath was removed
  2. stirringthe reaction mixture was stirred for 2 h
  3. additionThen, 50 ml of 2 M aqueous hydrogen chloride solution were added
  4. extractionthe mixture was extracted with dichloromethane
  5. customThe organic phase was dried
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0d6036023b0c46bf9521af566b4c467d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238631B2

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