Water → Ethyl 2-isopropoxy-3-[4-methoxy-3-({[2-fluoro-4-(trifluoromethyl)benzoyl]amino}methyl)phenyl]propanoate

HRID 1816573

Reaction equation

HRID 1816573 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([O:18][CH:19]([CH3:21])[CH3:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].N1C=CC=CC=1.[Cl-].[F:29][C:30]1[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[CH:35][C:31]=1[C:32]([O-])=[O:33].O>CN(C)C=O>[CH:19]([O:18][CH:12]([CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([CH2:2][NH:1][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][C:37]([C:39]([F:40])([F:41])[F:42])=[CH:38][C:30]=2[F:29])[CH:4]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 22493983Ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoateHCID 22494274HCID 22494274, compound

Product 1

HCID 22493991Ethyl 2-isopropoxy-3-[4-methoxy-3-({[2-fluoro-4-(trifluoromethyl)benzoyl]amino}methyl)phenyl]propanoateYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.15 g of ethyl 3-[3-(aminomethyl)-4-methoxyphenyl]-2-isopropoxypropanoate was dissolved in 5 ml N,N-dimethylformamide, and 0.2 ml pyridine and 0.24 g of 2-fluoro-4-(trifluoromethyl)benzoate chloride were added, followed by stirring at room temperature for 12 hours. Water was added to the reaction solution, followed by extracting with ethyl acetate The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with ethyl acetate-hexane (1:2), 0.2 g of ethyl 2-isopropoxy-3-[4-methoxy-3-({[2-fluoro-4-(trifluoromethyl)benzoyl]amino}methyl)phenyl]propanoate was obtained as a pale yellow oil. This product was treated in the same manner as in Example 1d), to give 0.15 g of 2-isopropoxy-3-[4-methoxy-3-{[2-fluoro-4-(trifluoromethyl)benzoyl]amino}methyl)phenyl]propanoic acid as a pale yellow solid.

Workup

  1. extractionby extracting with ethyl acetate The extract
  2. washwas washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washfrom fractions eluted with ethyl acetate-hexane (1:2)

Sources & evidence

ORD record
ord-ef68cc2d2d64433caca4d80357893d57
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Linked notes

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