3-Hydroxyanthranilic Acid → HCID 66620558, compound

HRID 415135

Reaction equation

HRID 415135 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[NH2:11].Cl[C:13]([C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]([CH3:31])[C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:17][CH:16]=1)=O.N1C=CC=CC=1.Cl.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH2:23]([O:22][C:21]([N:20]([CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[O:1][C:2]3[C:3](=[C:4]([C:5]([OH:7])=[O:6])[CH:8]=[CH:9][CH:10]=3)[N:11]=2)=[CH:33][CH:32]=1)[CH3:31])=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

9

Reactant 5

HCID 863-Hydroxyanthranilic AcidHCID 313Hydrochloric AcidHCID 1049PyridineHCID 6101p-Toluenesulfonic acidHCID 86633082HCID 86633082, compound

Product 1

HCID 66620558HCID 66620558, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-hydroxyanthranilic acid (0.300 g, 1.96 mmol) in toluene (10 mL) is added benzyl 4-(chlorocarbonyl)benzyl(methyl)carbamate (1.811 g, 5.7 mmol) followed by pyridine (0.545 g, 6.92 mmol) at room temperature. The resulting mixture is stirred at room temperature for 30 minutes then heated to 80° C. for 1 hr. After this time the reaction is cooled and poured into a mixture of ethyl acetate (50 mL) and 5% aqueous hydrochloric acid (50 mL). Subsequent separation of the layers, drying the organic over MgSO4 and filtration afford a solution. After removal of the solvent, the residue is dissolved in xylenes (20 mL) and the solution treated with p-TsOH (0.800 g, 4.20 mmol). The reaction mixture is then heated to reflux for 6 hrs. After this time the reaction is cooled and poured into water (50 mL), the organic layer is separated and then washed with water (3×50 mL). The organic is dried over MgSO4, filtered and concentrated to a solid. Flash column chromatography on silica gel using ethyl acetate and hexanes as the eluents gives a solid product, 2-(4-(((benzyloxycarbonyl)(methyl)amino)methyl)phenyl)benzo[d]oxazole-4-carboxylic acid. MS (ESI) m/e 417 [M+H]+.

Workup

  1. temperaturethen heated to 80° C. for 1 hr
  2. temperatureAfter this time the reaction is cooled
  3. customSubsequent separation of the layers
  4. customdrying the
  5. filtrationorganic over MgSO4 and filtration
  6. customafford a solution
  7. customAfter removal of the solvent
  8. dissolutionthe residue is dissolved in xylenes (20 mL)
  9. temperatureThe reaction mixture is then heated
  10. temperatureto reflux for 6 hrs
  11. temperatureAfter this time the reaction is cooled
  12. customthe organic layer is separated
  13. washwashed with water (3×50 mL)
  14. dry with materialThe organic is dried over MgSO4
  15. filtrationfiltered
  16. concentrationconcentrated to a solid

Sources & evidence

ORD record
ord-42da1ed535844ae5ab1c9d62310f4596
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Linked notes

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