(RS)-N-(4-cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamide → (RS)-{4-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-phenoxy}-acetic acid ethyl ester

HRID 1247267Notes

Reaction equation

HRID 1247267 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]([O:25][C:26](=[O:29])[CH2:27]Br)[CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:23]([O:25][C:26](=[O:29])[CH2:27][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:10]([C:9](=[O:20])[NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:22][CH:21]=2)[O:11][CH3:12])=[CH:14][CH:15]=1)[CH3:24]

Participants

4

Reactant 2

HCID 21905457(RS)-N-(4-cyano-benzyl)-2-(4-hydroxy-phenyl)-2-methoxy-acetamideHCID 86593044Ethylbromoacetate cesium carbonate

Product 1

HCID 69290182(RS)-{4-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-phenoxy}-acetic acid ethyl ester

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 (example 21.2) was alkylated with ethylbromoacetate/cesium carbonate in DMF to give (RS)-{4-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-phenoxy}-acetic acid ethyl ester as a colorless solid. MS 383.3 ([M+H]+)

Sources & evidence

ORD record
ord-7f174d3b95d643acaac0c75f9fbc97aa
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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