Benzyl Bromide → HCID 86602122, compound

HRID 16604Notes

Reaction equation

[CH3:1][C:2]([CH3:13])([C:8]1[NH:12][N:11]=[N:10][N:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH2:20]([N:10]1[N:11]=[N:12][C:8]([C:2]([CH3:1])([CH3:13])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:9]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred mixture of α,α-dimethyltetrazole-5-acetic acid, ethyl ester (J. Med. Chem. 1996, 39, 2354-2366.) (6.87 g, 37.3 mmol) and K2CO3 (12.3 g, 89.0 mmol) in acetone (200 mL) was added benzyl bromide (4.45 mL, 37.4 mmol) at ambient temperature. The resulting mixture was stirred at 50° C. for 18 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 6.14 g (60%) of the title compound as a colorless oil.

Workup

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

Sources & evidence

ORD record: ord-d53f1c9660474e9a883c9b1462b7325a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737163B2

Reaction notes

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