2,3-Dimethylbenzoic acid → Tert-butyl 2-(2,3-dimethylbenzamido)-4-(4-(tert-butoxycarbonyl)oxyphenyl)benzoate

HRID 1673441Notes

Reaction equation

HRID 1673441 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.[NH2:18][C:19]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:34][CH:33]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])O.[Na+]>C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[CH3:7][C:8]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:18][C:19]1[CH:31]=[C:30]([C:32]2[CH:33]=[CH:34][C:35]([O:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[CH:36][CH:37]=2)[CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:12]

Participants

8

Reactant 4

HCID 117822,3-Dimethylbenzoic acidHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 67344180Tert-butyl 2-amino-4-(4-(tert-butoxycarbonyl)oxyphenyl)benzoate

Product 1

HCID 67342726Tert-butyl 2-(2,3-dimethylbenzamido)-4-(4-(tert-butoxycarbonyl)oxyphenyl)benzoate

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

1.7 mL of methylene chloride, 1.0 μL of N,N-dimethylformamide and 0.025 mL of oxalyl chloride were added to 41 mg of 2,3-dimethylbenzoic acid at room temperature sequentially and stirred at the same temperature for 1 hour. The reaction mixture was added to a mixed solution of 62 mg of tert-butyl 2-amino-4-(4-(tert-butoxycarbonyl)oxyphenyl)benzoate, 2.8 mL of methylene chloride and 0.36 mL triethylamine and stirred at room temperature for 1 hour. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, and the organic layer was separated, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1] to obtain tert-butyl 2-(2,3-dimethylbenzamido)-4-(4-(tert-butoxycarbonyl)oxyphenyl)benzoate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. customthe organic layer was separated
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex Company, eluent; hexane; ethyl acetate=4:1]

Sources & evidence

ORD record
ord-a9b4ef0b96ae4047ab1397cfb76f5332
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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