Water → t-Butyl 4-(isopentylamino)methyl-3-nitrobenzoate

HRID 1953757Notes

Reaction equation

HRID 1953757 reaction equation
Br[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17].O>CN(C=O)C>[CH2:4]([NH:16][CH2:2][C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17])[CH2:5][CH:6]([CH3:14])[CH3:7]

Participants

4

Reactant 2

HCID 962WaterHCID 18462578t-Butyl 4-bromomethyl-3-nitrobenzoate

Product 1

HCID 23297798t-Butyl 4-(isopentylamino)methyl-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous isopentylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min. A solution of t-butyl 4-bromomethyl-3-nitrobenzoate (5.0 g, 15.8 mmol) (Int. J. Peptide. Res., 36, 31 (1990)) in DMF (10 mL) was added dropwise to the cold amine solution. The solution was stirred at 0° for 30 min and poured into water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with water, dried (sodium sulfate) and concentrated to give a yellow-brown oil. The oil was purified by chromatography over silica gel to yield t-butyl 4-(isopentylamino)methyl-3-nitrobenzoate.

Workup

  1. customAnhydrous isopentylamine was bubbled into anhydrous DMF (200 mL) at 0° C. for 15 min
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic layers were washed with water
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated
  6. customto give a yellow-brown oil
  7. customThe oil was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-36eb45eafb0d4ee894a9b5ec02fb4995
Source dataset
uspto-grants-2000_09
Patent number
US06117866

Reaction notes

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