Citric Acid → methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-3-yl)methyl]benzyl}amino)phenyl]propanoate

HRID 508028Notes

Reaction equation

HRID 508028 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:19][C:20]1[CH:51]=[CH:50][C:23]([CH2:24][N:25]([S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C:26]2[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[N+](C1C=CC=CC=1S(N(CC1C=CC(CN2C3C(=CC=CC=3)C=C2C2C=CC=CC=2)=CC=1)C1C=CC(CCC(OC)=O)=CC=1)(=O)=O)([O-])=O>CN(C)C=O.O>[N+:47]([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[S:38]([N:25]([CH2:24][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]=2[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[CH:51][CH:50]=1)[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])=[CH:28][CH:27]=1)(=[O:40])=[O:39])([O-:49])=[O:48]

Participants

8

Reactant 5

HCID 311Citric AcidHCID 136982-PhenylindoleHCID 24758Sodium hydrideHCID 23157281Methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateHCID 23157671methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate

Product 1

HCID 23157644methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-3-yl)methyl]benzyl}amino)phenyl]propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Under ice-cooling, sodium hydride (60% in oil, 0.436 g, 10.9 mmol) was added to a solution of 2-phenylindole (2.11 g, 10.9 mmol) in N,N-dimethylformamide (5 mL) by small portions, and the mixture was stirred under a nitrogen atmosphere at the same temperature for 1 hr. To the reaction mixture was added dropwise a solution of methyl 3-(4-{[4-(chloromethyl)benzyl][(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (3.65 g, 7.26 mmol) in N,N-dimethylformamide (5 mL), and the mixture was allowed to warm to room temperature and stirred for 3 hr. Water and 10% aqueous citric acid solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane) to give a mixture (1.53 g, yield 32%) of the title compound and methyl 3-[4-([(2-nitrophenyl)sulfonyl]{4-[(2-phenyl-1H-indol-1-yl)methyl]benzyl}amino)phenyl]propanoate as a brown oil.

Workup

  1. temperatureUnder ice-cooling
  2. stirringstirred for 3 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (20%-80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-17e33d8bea284175b70d036231d74c24
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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