(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide → (RS)-N-(2-carbamoylmethoxy-4-cyano-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide

HRID 1247355Notes

Reaction equation

HRID 1247355 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:15]=2[F:23])[O:11][CH2:12][CH3:13])=[C:5]([OH:27])[CH:4]=1)#[N:2].I[CH2:29][C:30]([NH2:32])=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:30]([CH2:29][O:27][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:26]=[CH:25][C:6]=1[CH2:7][NH:8][C:9](=[O:24])[CH:10]([C:14]1[C:15]([F:23])=[CH:16][C:17]([O:21][CH3:22])=[CH:18][C:19]=1[F:20])[O:11][CH2:12][CH3:13])(=[O:31])[NH2:32]

Participants

4

Reactant 2

HCID 21905119(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamideHCID 86593045Iodoacetamide cesium carbonate

Product 1

HCID 21905465(RS)-N-(2-carbamoylmethoxy-4-cyano-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 16.4, (RS)-N-(4-cyano-2-hydroxy-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide was alkylated with iodoacetamide/cesium carbonate in DMF to give (RS)-N-(2-carbamoylmethoxy-4-cyano-benzyl)-2-(2,6-difluoro-4-methoxy-phenyl)-2-ethoxy-acetamide as a colorless solid. MS 434.3 ([M+H]+)

Sources & evidence

ORD record
ord-d2e1068f848c4fe28f7b77082584c1ec
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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