(RS)-N-(4-cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamide → (RS)-N-(4-cyano-benzyl)-2-(4-ethoxy-phenyl)-2-methoxy-acetamide

HRID 1247260Notes

Reaction equation

HRID 1247260 reaction equation
[C:1]([C:3]1[CH:22]=[CH:21][C:6]([CH2:7][NH:8][C:9](=[O:20])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].[CH2:23](I)[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:20])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:23][CH3:24])=[CH:15][CH:14]=2)[O:11][CH3:12])=[CH:21][CH:22]=1)#[N:2]

Participants

4

Reactant 2

HCID 21905457(RS)-N-(4-cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamideHCID 86593038Ethyl iodide cesium carbonate

Product 1

HCID 21904945(RS)-N-(4-cyano-benzyl)-2-(4-ethoxy-phenyl)-2-methoxy-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 16.4, (RS)-N-(4-cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamide was alkylated with ethyl iodide/cesium carbonate in DMF to give (RS)-N-(4-cyano-benzyl)-2-(4-ethoxy-phenyl)-2-methoxy-acetamide as a colorless solid. MS 325.3 ([M+H]+)

Sources & evidence

ORD record
ord-ad7fb79c7cb84ca6ad55d45497ae8d30
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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