(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide → (RS)-(5-cyano-2-{[2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetylamino]-methyl)-phenoxy)-acetic acid ethyl ester

HRID 1247352Notes

Reaction equation

HRID 1247352 reaction equation
[C:1]([C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9](=[O:23])[CH:10]([O:20][CH2:21][CH3:22])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=2[F:19])=[C:5]([OH:26])[CH:4]=1)#[N:2].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][O:26][C:5]1[CH:4]=[C:3]([C:1]#[N:2])[CH:25]=[CH:24][C:6]=1[CH2:7][NH:8][C:9](=[O:23])[CH:10]([O:20][CH2:21][CH3:22])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=1[F:19])[CH3:33]

Participants

4

Reactant 2

HCID 21905309(RS)-N-(4-cyano-2-hydroxy-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamideHCID 86593044Ethylbromoacetate cesium carbonate

Product 1

HCID 69288832(RS)-(5-cyano-2-{[2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetylamino]-methyl)-phenoxy)-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to example 16.4, (RS)-N-(4-cyano-2-hydroxy-benzyl)-2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetamide (example 110.3) was alkylated with ethyl bromoacetate/cesium carbonate in DMF to give (RS)-(5-cyano-2-{[2-ethoxy-2-(2-fluoro-4-methoxy-phenyl)-acetylamino]-methyl}-phenoxy)-acetic acid ethyl ester as a colorless solid. MS 443.4 ([M−H])

Sources & evidence

ORD record
ord-d89ead26233b4ed2b95d7eb9afc8abc5
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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