1,5-Dibromopentane → HCID 67771842, compound

HRID 1720539Notes

Reaction equation

HRID 1720539 reaction equation
Cl.[C:2]([O:6][C:7](=[O:17])[C@H:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CN(C=O)C.C(OCC)C>[C:2]([O:6][C:7](=[O:17])[C@@H:8]([N:9]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 11459563L-Phenylalanine, 1,1-dimethylethyl ester, hydrochloride (1:1)

Product 1

HCID 67771842HCID 67771842, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of L-phenylalanine tert-butyl ester hydrochloride (3.05 g) in DMF (50 ml) were added potassium carbonate (5.38 g) and 1,5-dibromopentane (2.98 g), and the mixture was stirred at 80° C. for 2 hours, and then at room temperature for 22 hours. The reaction mixture was diluted with diethyl ether, washed with water and saturated brine successively, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (eluate: methylene chloride-methanol) to give 1.24 g of the title compound.

Workup

  1. waitat room temperature for 22 hours
  2. washwashed with water and saturated brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluate: methylene chloride-methanol)

Sources & evidence

ORD record
ord-76720852db524b9089a356057d8d91c0
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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