Water → tert-Butyl [(1-{[3-(aminocarbonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrol-3-yl)methyl]methylcarbamate

HRID 554357Notes

Reaction equation

HRID 554357 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22](O)=[O:23])(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([N:37]=C=NCCCN(C)C)C.[NH4+].ON1C2C=CC=CC=2N=N1.O>CN(C)C=O>[NH2:37][C:22]([C:21]1[CH:20]=[C:19]([S:16]([N:14]2[C:13]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:12][C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:15]2)(=[O:17])=[O:18])[CH:27]=[CH:26][CH:25]=1)=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 669249903-[(4-{[(tert-Butoxycarbonyl)(methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoic acid

Product 1

HCID 66925192tert-Butyl [(1-{[3-(aminocarbonyl)phenyl]sulfonyl}-5-phenyl-1H-pyrrol-3-yl)methyl]methylcarbamateYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (5 mL) of 3-[(4-{[(tert-butoxycarbonyl)(methyl)amino]methyl}-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzoic acid (205 mg) in N,N-dimethylformamide were added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (125 mg) and 1-hydroxy-1H-benzotriazole ammonium salt (100 mg) at room temperature. The mixture was stirred at the same temperature for 1 hr, water was added and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1→1:4) to give the title compound as a colorless oil (yield 193 mg, 94%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1→1:4)

Sources & evidence

ORD record
ord-d9c6ee3469ba4e75a2dcfb40aa906e0b
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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