Triethylamine → Methyl N-{4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)-benzoyl}glycinate

HRID 1692568Notes

Reaction equation

HRID 1692568 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[Cl:27][C:28]1[CH:29]=[C:30]([C:36]2([C:54]([F:57])([F:56])[F:55])[CH2:40][C:39]([C:41]3[CH:49]=[CH:48][C:44]([C:45](O)=[O:46])=[C:43]([C:50]([F:53])([F:52])[F:51])[CH:42]=3)=[N:38][CH2:37]2)[CH:31]=[C:32]([Cl:35])[C:33]=1[Cl:34]>CN(C)C=O.C(OC)(C)(C)C>[Cl:27][C:28]1[CH:29]=[C:30]([C:36]2([C:54]([F:55])([F:57])[F:56])[CH2:40][C:39]([C:41]3[CH:49]=[CH:48][C:44]([C:45]([NH:2][CH2:3][C:4]([O:6][CH3:7])=[O:5])=[O:46])=[C:43]([C:50]([F:51])([F:52])[F:53])[CH:42]=3)=[N:38][CH2:37]2)[CH:31]=[C:32]([Cl:35])[C:33]=1[Cl:34]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 582709924-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acid

Product 1

HCID 58270969Methyl N-{4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)-benzoyl}glycinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To the solution of methyl glycinate hydrochloride (0.36 g, 2.89 mmol) in N,N-dimethylformamide was added triethylamine (0.59 g, 5.78 mmol) at 0° C. Then 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (0.40 g, 1.73 mmol), 4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acid (0.73 g, 1.44 mmol) was added to the solution. Reaction mixture was stirred for overnight at room temperature. The reaction mixture was diluted with t-BuOMe, washed with H2O, and dried over MgSO4. After evaporation, the residue was purified by column chromatography (0.13 g, 16%).

Workup

  1. customReaction mixture
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. customAfter evaporation
  5. customthe residue was purified by column chromatography (0.13 g, 16%)

Sources & evidence

ORD record
ord-cde2d91344a44e9c8d31a5fb3d34632c
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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