Benzyl Bromide → HCID 86607414, compound

HRID 733102Notes

Reaction equation

HRID 733102 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[C:6]1[NH:10][N:9]=[N:8][N:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([N:8]1[N:9]=[N:10][C:6]([CH:5]([CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15]2)[C:4]([O:3][CH2:1][CH3:2])=[O:16])=[N:7]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178470802HCID 178470802, compound

Product 1

HCID 86607414HCID 86607414, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of α-cyclopentyltetrazole-5-acetic acid, ethyl ester (step 1 of Example 14) and K2CO3 (12.3 g, 89.0 mmol) in acetone (200 mL) was added benzyl bromide (4.84 mL, 40.7 mmol) at ambient temperature. The resulting mixture was stirred at 50° C. for 14 h and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (10:1) to give 2.95 g (27% in 2 steps) of the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-eda8cbf177264e4b9be9ff6318a2273b
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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