Cesium carbonate → 4-Chloro-2-[[2-chloro-4-(ethylsulfonyl)phenyl]amino]-benzenepropanoic acid

HRID 910871Notes

Reaction equation

HRID 910871 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][C:15]=2[Cl:24])[CH:3]=1.[CH2:25](S(C1C=CC(F)=C(Cl)C=1)(=O)=O)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH2:23][CH3:25])(=[O:21])=[O:22])=[CH:16][C:15]=2[Cl:24])[CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 115528094-Chloro-2-[[2-chloro-4-(methylsulfonyl)phenyl]amino]-benzenepropanoic acidHCID 579047252-Chloro-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 115821354-Chloro-2-[[2-chloro-4-(ethylsulfonyl)phenyl]amino]-benzenepropanoic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of the product from example 49 step (iii) (0.163 g) and the product of example 4 step (i) (0.200 g) and caesium carbonate (0.239 g) in NMP (10 ml) was refluxed at 100° C. for 3 hours. The mixture was partitioned between 2M sodium hydroxide and diethyl ether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate and the organic layer dried and concentrated under reduced pressure to give an oil. The residue was purified using RP prep HPLC. Yield 0.044 g.

Workup

  1. customThe mixture was partitioned between 2M sodium hydroxide and diethyl ether
  2. extractionextracted with ethyl acetate
  3. customthe organic layer dried
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThe residue was purified

Sources & evidence

ORD record
ord-07ab93282da34d8aa8ac9937edbc7608
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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