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Triethylamine → Ethyl 2-isopropoxy-3-[4-methoxy-3-(4-trifluoromethylphenylacetylamino)phenyl]propanoate

HRID 1816556
Notes
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Reaction equation

HRID 1816556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][CH:11]([O:17][CH:18]([CH3:20])[CH3:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.C(N(CC)CC)C>O1CCCC1.O>[CH:18]([O:17][CH:11]([CH2:10][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([NH:1][C:30](=[O:31])[CH2:29][C:26]2[CH:25]=[CH:24][C:23]([C:22]([F:33])([F:21])[F:34])=[CH:28][CH:27]=2)[CH:3]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])([CH3:19])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 22494286Ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate

Product 1

HCID 22494218Ethyl 2-isopropoxy-3-[4-methoxy-3-(4-trifluoromethylphenylacetylamino)phenyl]propanoateYield 68.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

0.3 g of ethyl 3-(3-amino-4-methoxyphenyl)-2-isopropoxypropanoate and 0.218 g of (α,α,α-trifluoro-p-tolyl)acetic acid were dissolved in 7 ml tetrahydrofuran, and 0.22 g of carbonyldiimidazole and 0.23 ml triethylamine were added thereto, and the mixture was stirred at 50° C. for 2 hours. The reaction mixture was ice-cooled, and water was added followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (6:1), 0.34 g of ethyl 2-isopropoxy-3-[4-methoxy-3-(4-trifluoromethylphenylacetylamino)phenyl]propanoate was obtained.

Workup

  1. temperaturecooled
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washfrom fractions eluted with hexane-ethyl acetate (6:1)

Sources & evidence

ORD record
ord-cd9261a483e94742b7b1dbf57b5613be
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884821B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes