(4-Chlorophenyl)acetic acid → HCID 21962892, compound

HRID 2212002Notes

Reaction equation

HRID 2212002 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:5][N:6]1[C:11]([CH3:13])([CH3:12])[CH2:10][O:9][CH:8]([CH2:14][NH2:15])[CH2:7]1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1>CN1CCCC1=O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([NH:15][CH2:14][CH:8]2[O:9][CH2:10][C:11]([CH3:13])([CH3:12])[N:6]([CH2:5][C:4]3[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Cl:1])[CH:3]=3)[CH2:7]2)=[O:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 15880(4-Chlorophenyl)acetic acidHCID 21962913HCID 21962913, compound

Product 1

HCID 21962892HCID 21962892, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of Intermediate 3 (0.030 g) and 4-chlorophenylacetic acid (0.020 g) were treated with 1-methyl-2-pyrrolidinone (0.015 ml) then heated in a 600 W microwave oven, at full power, for 4 min. The crude mixture was purified by chromatography on silica gel (Varian Bond-Elut cartridge, 1 g) eluting with cyclohexane/ethyl acetate (19:1 followed by 1:1) to give a brown solid which was triturated with ether to give thetitle compound as an off-white solid (0.018 g).

Workup

  1. temperaturethen heated in a 600 W microwave oven, at full power, for 4 min
  2. customThe crude mixture was purified by chromatography on silica gel (Varian Bond-Elut cartridge, 1 g)
  3. washeluting with cyclohexane/ethyl acetate (19:1 followed by 1:1)
  4. customto give a brown solid which
  5. customwas triturated with ether

Sources & evidence

ORD record
ord-ccf177a23ecd4ce5aa974d73200a5a8d
Source dataset
uspto-grants-2006_09
Patent number
US07101882B2

Reaction notes

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