Hydrochloric Acid → Tert-butyl 2-(biphenyl-3-carboxamido)-4-phenoxybenzoate

HRID 1673539Notes

Reaction equation

HRID 1673539 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=O)[CH:8]=1.[NH2:22][C:23]1[CH:35]=[C:34]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:32][C:24]=1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].Cl>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl>[C:7]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([NH:22][C:23]2[CH:35]=[C:34]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:33]=[CH:32][C:24]=2[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])=[O:15])[CH:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 12854(1,1'-Biphenyl)-3-carboxylic acidHCID 65578Oxalyl chlorideHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67344270Tert-butyl 2-(biphenyl-3-carboxamido)-4-phenoxybenzoateYield 6.6%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

4.0 mL of methylene chloride, 0.015 mL of N-dimethylformamide and 0.050 mL of oxalyl chloride were added to 99 mg of 3-biphenylcarboxylic acid at room temperature sequentially and stirred at the same temperature for 20 minutes. 0.16 mL of triethylamine and 0.13 g of tert-butyl 2-amino-4-phenoxybenzoate were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 10 minutes. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform] to obtain 14 mg of tert-butyl 2-(biphenyl-3-carboxamido)-4-phenoxybenzoate as white solid.

Workup

  1. stirringstirred at the same temperature for 10 minutes
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with a saturated sodium chloride aqueous solution
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; chloroform]

Sources & evidence

ORD record
ord-806b55725c3c45abbd4b065f9640584e
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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