Triethylamine → [2'-({[2-(4-Chloro-phenoxy)-2-methyl-propionyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 2197352Notes

Reaction equation

HRID 2197352 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C:7]([CH3:12])([CH3:11])[C:8](Cl)=[O:9])=[CH:4][CH:3]=1.[CH3:15][O:16][C:17](=[O:41])[CH2:18][C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:28]=2[CH2:37][NH:38][CH2:39][CH3:40])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:15][O:16][C:17](=[O:41])[CH2:18][C:19]1[CH:20]=[C:21]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:29][C:28]=2[CH2:37][N:38]([C:8](=[O:9])[C:7]([O:6][C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=2)([CH3:12])[CH3:11])[CH2:39][CH3:40])[C:22]([O:25][CH3:26])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27813122-(4-Chlorophenoxy)-2-methylpropanoyl chlorideHCID 66603748(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66604389[2'-({[2-(4-Chloro-phenoxy)-2-methyl-propionyl]-ethyl-amino}-methyl)-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-phenoxy)-2-methyl-propionyl chloride (0.58 mmol) in CH2Cl2 was added (2′-ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.200 g, 0.52 mmol) in triethylamine (0.17 mL, 1.23 mmol), and the reaction was stirred at room temperature for 30 minutes. The mixture was concentrated and purified by silica gel chromatography (10-30% EtOAc in hexanes) to give [2′-({[2-(4-chloro-phenoxy)-2-methyl-propionyl]-ethyl-amino}-methyl)-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester. The ester was hydrolyzed according to the procedure described in Example 9, Step 2.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography (10-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-47461283a504463685f48fb534c055fd
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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