Sodium Hydroxide → 3-Oxo-3-(3-[1,2,3)triazol-1-yl-phenyl)-propionic acid ethyl ester

HRID 1265584Notes

Reaction equation

HRID 1265584 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)[CH:5]=[CH:4][N:3]=[N:2]1.N(C1C=C(C=CC=1)C(OC)=O)=[N+]=[N-].[OH-].[Na+].ClC(OCC)=O.CCN(CC)CC.[K+].[C:44]([O:50][CH2:51][CH3:52])(=[O:49])[CH2:45]C([O-])=O.[Mg+2].[Cl-].[Cl-]>C[Si](C#C)(C)C.CC#N.CCN(CC)CC.CCO>[CH2:51]([O:50][C:44](=[O:49])[CH2:45][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)[CH:7]=1)[CH3:52]

Participants

11

Reactant 6

HCID 14798Sodium HydroxideHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 11240787Methyl 3-azidobenzoateHCID 19692316ethyl chloroformate Et3NHCID 222248533-(1H-1,2,3-triazol-1-yl)benzoic acid

Product 1

HCID 695928683-Oxo-3-(3-[1,2,3)triazol-1-yl-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 66111TrimethylsilylacetyleneSolvent

Procedure

The title compound was prepared from 3-[1,2,3]triazol-1-yl-benzoic acid, prepared by refluxing of methyl 3-azidobenzoate [CAS-No. 93066-93-41] in trimethylsilyl-acetylene, followed by saponification with aqueous NaOH in refluxing EtOH] by activation with ethyl chloroformate/Et3N and reaction with ethyl malonate potassium salt with Et3N and MgCl2 in CH3CN according to general procedure K (method a). Obtained as a light yellow solid (2.22 g).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-674e5678ad54499787971d9bc22aff7e
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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