Citric Acid → HCID 66990230, compound

HRID 454592Notes

Reaction equation

HRID 454592 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[NH2:9][C:10]1[CH:37]=[CH:36][C:13]([C:14]([NH:16][C:17]2[CH:29]=[C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[CH:26][C:18]=2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15])=[C:12]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:11]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[CH3:59][N:60]([CH3:64])[C:61](=O)[CH3:62]>C(OCC)(=O)C>[CH2:39]([O:38][C:12]1[CH:11]=[C:10]([NH:9][CH3:1])[CH:37]=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[O:15])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[CH2:39]([O:38][C:12]1[CH:11]=[C:61]([N:60]([CH3:64])[CH3:59])[CH:62]=[CH:36][C:13]=1[C:14]([NH:16][C:17]1[CH:29]=[C:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[CH:26][C:18]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:15])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

8

Reactant 5

HCID 311Citric AcidHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 31374DimethylacetamideHCID 66989968HCID 66989968, compound

Product 2

HCID 66990230HCID 66990230, compoundHCID 66990514HCID 66990514, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (0.084 g) and methyl iodide (0.028 mL) were added to an N,N-dimethylacetamide (1.5 mL) solution of tert-butyl 2-(4-amino-2-(benzyloxy)benzamido)-4-phenylbenzoate (0.15 g), followed by stirring at room temperature for 1 hour and then at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and then potassium carbonate (0.042 g) and methyl iodide (0.019 mL) were added thereto, followed by stirring at 80° C. for 20 minutes. The reaction mixture was cooled to room temperature, and a 10% aqueous solution of citric acid and ethyl acetate were added thereto. The organic layer was separated, washed with a 10% aqueous solution of citric acid and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate] to obtain 0.056 g of tert-butyl 2-(2-(benzyloxy)-4-(methylamino)benzamido)-4-phenylbenzoate as a white solid and 0.049 g of tert-butyl 2-(2-(benzyloxy)-4-(dimethylamino)benzamido)-4-phenylbenzoate as a white solid.

Workup

  1. waitat 80° C. for 30 minutes
  2. temperatureThe reaction mixture was cooled to room temperature
  3. stirringby stirring at 80° C. for 20 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. washwashed with a 10% aqueous solution of citric acid
  7. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [eluent: 90-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-f03ce54a21f345eeaf1f4c23a9a5fd6e
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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