Hydrochloric Acid → tert-butyl 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoate

HRID 1673538Notes

Reaction equation

HRID 1673538 reaction equation
C(Cl)(=O)C(Cl)=O.[N:7]1([C:12]2[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=2)[C:15]([OH:17])=O)[CH:11]=[CH:10][CH:9]=[CH:8]1.[NH2:21][C:22]1[CH:34]=[C:33]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=[CH:31][C:23]=1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].Cl>C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)Cl.CN(C)C=O>[O:35]([C:33]1[CH:32]=[CH:31][C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[C:22]([NH:21][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][CH:20]=[C:12]([N:7]3[CH:8]=[CH:9][CH:10]=[CH:11]3)[CH:13]=2)[CH:34]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 7365373-(1H-pyrrol-1-yl)benzoic acidHCID 58508592Tert-butyl 2-amino-4-phenoxybenzoate

Product 1

HCID 67344182tert-butyl 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoate

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.015 mL of N,N-dimethylformamide was added to a mixed solution of 2.0 mL of methylene chloride and 0.024 mL of oxalyl chloride containing 47 mg of 3-(1H-pyrrol-1-yl)benzoic acid and stirred at room temperature for 30 minutes, 71 mg of tert-butyl 2-amino-4-phenoxybenzoate and 0.090 mL of triethylamine were added to the reaction mixture at room temperature sequentially and stirred at the same temperature for 30 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; hexane:ethyl acetate=40:1] to obtain 31 mg of tert-butyl 4-phenoxy-2-(3-(1H-pyrrol-1-yl)benzamido)benzoate as white solid.

Workup

  1. stirringstirred at the same temperature for 30 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; hexane:ethyl acetate=40:1]

Sources & evidence

ORD record
ord-662844624e2c40498300610e08fd6568
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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