Benzyl Bromide → Phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate

HRID 2367089Notes

Reaction equation

HRID 2367089 reaction equation
[C:1]([CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([OH:18])=[O:17])=[O:13])=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])([OH:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C)C=O.C(OCC)(=O)C>[N+:23]([C:7]1[CH:8]=[C:9]([C:12]([C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[C:16]([O:18][CH2:12][C:9]2[CH:10]=[CH:11][CH:6]=[CH:7][CH:8]=2)=[O:17])=[O:13])[CH:10]=[CH:11][C:6]=1[NH:5][CH2:4][C:1](=[O:3])[O:2][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 670441602-({4-[(Carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid

Product 1

HCID 67045250Phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoateYield 165.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-({4-[(carboxymethyl)amino]-3-nitrophenyl}carbonyl)benzoic acid (0.26 g, 0.76 mmol) in N,N-dimethyl formamide (5.0 mL), potassium carbonate (0.52 g, 3.80 mmol) was added, followed by the addition of benzyl bromide (0.22 mL, 1.82 mmol). The reaction mixture was stirred for 15 hours at room temperature. It was poured into ice water and diluted with ethyl acetate (50 mL). The organic layer was separated and it was washed with water, 2M aqueous hydrochloric acid and brine. It was dried over anhydrous sodium sulfate. Evaporating the solvent, followed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 3:2 eluent) resulted in phenylmethyl 2-{[3-nitro-4-({2-oxo-2-[(phenylmethyl)oxy]ethyl}amino)phenyl]carbonyl}benzoate (0.33 g, 82% yield) as an amorphous residue. MS (EI) for C30H24N2O7: 524 (MH+).

Workup

  1. customThe organic layer was separated
  2. washit was washed with water, 2M aqueous hydrochloric acid and brine
  3. dry with materialIt was dried over anhydrous sodium sulfate
  4. customEvaporating the solvent
  5. customfollowed by purification of the crude product by silica gel flash chromatography (hexane:ethyl acetate 4:1 to 3:2 eluent)

Sources & evidence

ORD record
ord-9a003baa69394a778ea1d36ddf63e88f
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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