Water → HCID 69070098, compound

HRID 2110016Notes

Reaction equation

HRID 2110016 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:6]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20])[CH:5]=1.[C:32](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:31])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])=[C:6]([N:18]([CH3:32])[S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 69063936HCID 69063936, compound

Product 1

HCID 69070098HCID 69070098, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-tert-butoxycarbonylamino-3-(2-nitro-benzenesulfonylamino)-benzoic acid methyl ester (1.23 g, 2.73 mmol) in dimethylformamide (10 ml), potassium carbonate (1.13 g, 8.16 mmol) and methyl iodide (0.254 ml, 4.09 mmol) were added in an ice bath, and the mixture was stirred at room temperature for 2 hours. Water (100 ml) was added to the reaction mixture, and extraction was performed with ethyl acetate (40 ml×4 times). The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the crystallized residue was dried to obtain 4-tert-butoxycarbonylamino-3-[methyl-(2-nitro-benzenesulfonyl)-amino]-benzoic acid methyl ester. The compound was identified by LC-MS.

Workup

  1. additionwere added in an ice bath
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe crystallized residue was dried

Sources & evidence

ORD record
ord-a877cb0a548e44e6bed30c3415bb7164
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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