1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl 3-(azidomethyl)-5-(N-methylmethylsulfonamido)benzoate

HRID 2070959Notes

Reaction equation

O[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([CH3:18])[S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].C1(P([N:33]=[N+:34]=[N-:35])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.C1COCC1>[N:33]([CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]([CH3:18])[S:14]([CH3:17])(=[O:16])=[O:15])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=[N+:34]=[N-:35]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirring solution of 130 mg (0.475 mmol) of methyl 3-(hydroxymethyl)-5-(N-methylmethylsulfonamido)benzoate in 7 mL of toluene and 4 mL of THF was added 120 μL of diphenyl phosphoryl azide (DPPA). The solution was cooled to 0° C. and 86 μL (0.568 mmol) of 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) was added. The ice bath was removed, and stirring was continued with warming to room temperature. After about 16 h, the solution was diluted with EtOAc and H2O, and 1N HCl was added to a pH=8. The organic layer was washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was purified by flash silica gel chromatography (50% EtOAc/hexanes) to give 151 mg of methyl 3-(azidomethyl)-5-(N-methylmethylsulfonamido)benzoate as a yellow oil.

Workup

customThe ice bath was removed
temperaturewith warming to room temperature
additionthe solution was diluted with EtOAc and H2O, and 1N HCl
additionwas added to a pH=8
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationAfter filtration and concentration
customthe crude product was purified by flash silica gel chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-a5177ae5901349399e777fbf134f3567
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299267B2

Reaction notes

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