Water → 4-Tert-butoxycarbonylamino-3-methylaminobenzoic acid methyl ester

HRID 2110017Notes

Reaction equation

HRID 2110017 reaction equation
[CH3:1][O:2][C:3](=[O:32])[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]([N:18]([CH3:31])S(C2C=CC=CC=2[N+]([O-])=O)(=O)=O)[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].C1(S)C=CC=CC=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])=[C:6]([NH:18][CH3:31])[CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 69070098HCID 69070098, compound

Product 1

HCID 690638464-Tert-butoxycarbonylamino-3-methylaminobenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving 4-tert-butoxycarbonylamino-3-[methyl-(2-nitro-benzenesulfonyl)-amino]-benzoic acid methyl ester (1.41 g, 2.73 mmol) in dimethylformamide (10 ml), potassium carbonate (1.13 g, 8.16 mmol) and thiophenol (0.307 ml, 2.99 mmol) were added in an ice bath, and the mixture was stirred at room temperature for 1 hour. Water (100 ml) was added to the reaction mixture, and extraction was performed with ethyl acetate (40 ml×3 times). The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (n-hexane/ethyl acetate=85/15) to obtain 4-tert-butoxycarbonylamino-3-methylamino-benzoic acid methyl ester. The compound was identified by LC-MS. Yield: 794.3 mg (62.7%), [M+1]=281.1.

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. customThe residue obtained by concentration under reduced pressure
  5. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-dc18e1e762c148d899bb824362af408a
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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