Triethylamine → 3-(2-Methyl-4-{[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-carbamoyl}-phenyl)-propionic acid ethyl ester

HRID 854564Notes

Reaction equation

HRID 854564 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:17][NH2:18].[C:19]([CH2:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][C:25]=1[CH3:33])([OH:21])=[O:20].[CH2:34](N(CC)CC)[CH3:35].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:34]([O:21][C:19](=[O:20])[CH2:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](=[O:30])[NH:18][CH2:17][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:26][C:25]=1[CH3:33])[CH3:35]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 58765787C-[5-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-methylamineHCID 694730814-(2-Carboxy-ethyl)-3-methyl-benzoic acid

Product 1

HCID 694707913-(2-Methyl-4-{[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-carbamoyl}-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of C-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-yl]-methylamine (0.2 g, 0.78 mmol) and 4-(2-carboxy-ethyl)-3-methyl-benzoic acid (0.173 g, 0.78 mmol) and DMAP (5 mg) in methylene chloride (5 mL) are added triethyl amin (0.12 mL, 0.86 mml) and EDCI (150 mg, 0.78 mmol) at room temperature. After stirred for 3 hrs, diluted with chloroform, washed with water, 1N HCl and 2 N NaOH aqueous. Concentration and column chromatography on silica gel gave the title compound (240 mg).

Workup

  1. washwashed with water, 1N HCl and 2 N NaOH aqueous
  2. concentrationConcentration and column chromatography on silica gel

Sources & evidence

ORD record
ord-e7239e7ef55f4c18bc06ec2520623b1b
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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