Water → HCID 66738209, compound

HRID 1641812Notes

Reaction equation

HRID 1641812 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([C@@H:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[C:24]([OH:26])=[O:25])=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[CH3:29][N:16]([C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[CH:11][CH:12]=1)[C:17]([C@@H:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[C:24]([OH:26])=[O:25])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66738359HCID 66738359, compound

Product 1

HCID 66738209HCID 66738209, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of rac-trans-2-(4′-nitro-biphenyl-4-ylcarbamoyl)-cyclopentanecarboxylic acid (3.54 g, 10 mmol) in DMF cooled at 0° C. was added sodium hydride (0.48 g, 12 mmol) gradually. The mixture was stirred at room temperature for 15 min followed by the addition of methyl iodide (0.7 mL). The reaction mixture was stirred for 2 h. The reaction was then mixed with water and extracted with ethyl acetate. The organic layer was washed with water and brine. The organic layer dried over sodium sulfate, filtered and concentrated to give rac-trans-2-[methyl-(4′-nitro-biphenyl-4-yl)-carbamoyl]-cyclopentanecarboxylic acid as a yellow solid. With a method similar to that used above, trans-2-[(4′-amino-biphenyl-4-yl)-methyl-carbamoyl]-cyclopentanecarboxylic acid was prepared by the hydrogenation of trans-2-[methyl-(4′-nitro-biphenyl-4-yl)-carbamoyl]-cyclopentanecarboxylic acid. This material was directly used in the next step without further purification. LCMS calcd for C20H22N2O3 (m/e) 338, obsd 339 (M+H).

Workup

  1. stirringThe reaction mixture was stirred for 2 h
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialThe organic layer dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e18f81b069a41669ecf6d3b014abaa6
Source dataset
uspto-grants-2012_02
Patent number
US08115011B2

Reaction notes

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