Cesium carbonate → 3-[4-(3-Methyl-4'-trifluoromethyl-biphenyl-4-ylmethoxy)-benzoylamino]-propionic acid methyl ester

HRID 1669262Notes

Reaction equation

HRID 1669262 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[CH:21][C:20]=1[CH3:35].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.O>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][NH:6][C:7](=[O:15])[C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=3)=[CH:21][C:20]=2[CH3:35])=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 106328533-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 222801404-Chloromethyl-3-methyl-4'-trifluoromethyl-biphenyl

Product 1

HCID 673435023-[4-(3-Methyl-4'-trifluoromethyl-biphenyl-4-ylmethoxy)-benzoylamino]-propionic acid methyl esterYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (0.11 g, 0.49 mmol) and 4-chloromethyl-3-methyl-4′-trifluoromethyl-biphenyl (0.12 g, 0.41 mmol) in acetonitrile (4 mL) is added Cs2CO3 (0.20 g, 0.61 mmol). The mixture is stirred at RT for 12 h. The mixture is diluted with water and extracted with EtOAc. The organics are dried with MgSO4, and the crude material is purified by flash chromatography to yield 0.11 g (58%) of the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organics are dried with MgSO4
  3. customthe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-df796200462b48c78c7d863b62437cc2
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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