2,4-Dichlorobenzoic Acid → HCID 22926951, compound

HRID 1985430Notes

Reaction equation

HRID 1985430 reaction equation
[NH2:1][O:2][C:3]1[CH:4]=[C:5]([C:9](OC(C)C)(C)[C:10]([O-:12])=O)[CH:6]=[CH:7][CH:8]=1.[Cl:18][C:19]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21]([OH:23])=O.[C-:29]#N.P(=O)([O:35][CH2:36][CH3:37])OCC.C(N([CH2:44][CH3:45])CC)C.CN(C)[CH:48]=[O:49]>C(OCC)(=O)C>[Cl:18][C:19]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:20]=1[C:21]([NH:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([O:12][CH:44]([CH3:45])[CH3:29])[C:48]([O:35][CH2:36][CH3:37])=[O:49])[CH:6]=[CH:7][CH:8]=1)=[O:23]

Participants

7

Reactant 5

HCID 57872,4-Dichlorobenzoic AcidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 86592578HCID 86592578, compoundHCID 178476837HCID 178476837, compound

Product 1

HCID 22926951HCID 22926951, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 mg of Ethyl 3-(3-aminooxyphenyl-2-isopropoxypropionate and 7 mg of 2,4-dichlorobenzoic acid were dissolved in 0.3 ml of N,N-dimethylformamide, 0.006 ml of diethyl phosphonate cyanide and 0.05 ml of triethylamine were added, and the mixture was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate and washed with water. The organic layer was concentrated, to give ethyl 3-[3-(2,4-dichlorobenzoylaminooxy)phenyl]-2-isopropoxypropionate. This product was then dissolved in 0.4 ml of ethanol, 0.1 ml of 5N sodium hydroxide was added, and the mixture was stirred overnight at room temperature. The reaction solution was treated with 1N hydrochloric acid, extracted with ethyl acetate, and the organic layer was concentrated. The residue was purified by reverse-phase high performance liquid chromatography, to give the title compound.

Workup

  1. washwashed with water
  2. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-62ec0cd81aaf4428bca06cb0b3ae9cbb
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

Loading…