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

HRID 2070959
Notes
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Reaction equation

HRID 2070959 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 57815142Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate

Product 1

HCID 86647414methyl 3-(azidomethyl)-5-(N-methylmethylsulfonamido)benzoate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8028
Tetrahydrofuran
Solvent

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

  1. customThe ice bath was removed
  2. temperaturewith warming to room temperature
  3. additionthe solution was diluted with EtOAc and H2O, and 1N HCl
  4. additionwas added to a pH=8
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtration and concentration
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes