Pyridine → HCID 69063936, compound

HRID 2110015Notes

Reaction equation

HRID 2110015 reaction equation
[CH3:1][O:2][C:3](=[O:19])[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]([NH2:18])[CH:5]=1.N1C=CC=CC=1.[N+:26]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[S:35](Cl)(=[O:37])=[O:36])([O-:28])=[O:27]>ClCCl>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])=[C:6]([NH:18][S:35]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N+:26]([O-:28])=[O:27])(=[O:36])=[O:37])[CH:5]=1

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 155402-Nitrobenzenesulfonyl chloride2×HCID 18621647Methyl 3-amino-4-[(tert-butoxycarbonyl)amino]benzoate

Product 1

HCID 69063936HCID 69063936, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving 3-amino-4-tert-butoxycarbonylaminobenzoic acid methyl ester (817.3 mg, 3.07 mmol) in dichloromethane (10 ml), pyridine (0.373 ml, 4.60 mmol) and 2-nitrobenzenesulfonyl chloride (815 mg, 3.68 mmol) were added in an ice bath, and the mixture was stirred at room temperature for 4 hours. Pyridine (0.050 ml) and 2-nitrobenzenesulfonyl chloride (135 mg) were added, and stirring was continued for 2 hours. The reaction mixture was concentrated under reduced pressure, water (30 ml) was added, and then extraction was performed with ethyl acetate (20 ml×3 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 suspended in n-hexane-ethyl acetate (4:1), filtered, and dried to obtain 4-tert-butoxycarbonylamino-3-(2-nitro-benzenesulfonylamino)-benzoic acid methyl ester. The compound was identified by LC-MS.

Workup

  1. additionwere added in an ice bath
  2. stirringstirring
  3. waitwas continued for 2 hours
  4. concentrationThe reaction mixture was concentrated under reduced pressure, water (30 ml)
  5. additionwas added
  6. extractionextraction
  7. washThe obtained organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationAfter concentration under reduced pressure
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-8f950a557c6748329d431bf03c815f56
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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