Acetic Acid → HCID 90052209, compound

HRID 2284668Notes

Reaction equation

HRID 2284668 reaction equation
[C:1]([NH:8][CH2:9][C:10](O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([NH2:23])[CH:17]=1)([O-:15])=[O:14].C(O)(=O)C.O>O1CCCC1.ClC(OCC(C)C)=O.CN1CCOCC1.C(OCC)(=O)C>[N+:13]([C:16]1[CH:21]=[CH:20][C:19]2[N:22]=[C:10]([CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[NH:23][C:18]=2[CH:17]=1)([O-:15])=[O:14]

Participants

9

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 78288N-(tert-butoxycarbonyl)glycineHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 90052209HCID 90052209, compoundYield 82.1%

Reagents, catalysts & solvents 4

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-glycine (571 mg) in tetrahydrofuran (16 mL), isobutyl chloroformate (428 μL) and N-methylmorpholine (358 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 20 minutes. To the reaction mixture, 4-nitro-1,2-phenylenediamine (500 mg) was added under ice cooling, and the mixture was stirred at room temperature for 3 hours and 30 minutes. To the reaction mixture, acetic acid (16 mL) was added, and the mixture was stirred at 70° C. for 3 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate) to obtain tert-butyl ((6-nitro-1H-benzo[d]imidazol-2-yl)methyl)carbamate (C19, 782 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours and 30 minutes
  2. stirringthe mixture was stirred at 70° C. for 3 hours and 30 minutes
  3. customThe organic layer was separated
  4. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-28c4baa53ff04c01a836f5406c058878
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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