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

HRID 591331Notes

Reaction equation

HRID 591331 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 117778092HCID 117778092, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0d6036023b0c46bf9521af566b4c467d
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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