Water → HCID 86583546, compound

HRID 1841739Notes

Reaction equation

HRID 1841739 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([S:23][CH3:24])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH:31](I)([CH3:33])[CH3:32].O>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH:31]([CH3:33])[CH3:32])=[C:18]([S:23][CH3:24])[CH:17]=2)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 86583544HCID 86583544, compound

Product 1

HCID 86583546HCID 86583546, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of the ethyl (RS)-(4-cyano-phenylamino)-(4-hydroxy-3-methylsulphanyl-phenyl)-acetate (198 mg, 0.58 mmol) described in Example 168.1, Cs2CO3 (227 mg, 0.64 mmol) and isopropyl iodide (58 μl, 0.58 mmol) in acetone (3 ml) was heated under reflux for 4 h. Water was added and the mixture was extracted with CH2Cl2. Die organic phase was dried, filtered and concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 2:1). Ethyl (RS)-(4-cyano-phenylamino)-(4-isopropoxy-3-methylsulphanyl-phenyl)-acetate (140 mg, 63%) was obtained as a colorless oil; MS: 443 ([M+OAc]−).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. extractionthe mixture was extracted with CH2Cl2
  4. customDie organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (SiO2, hexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-695b703996a5424cafcf95b3a0be2166
Source dataset
uspto-grants-2004_01
Patent number
US06683215B2

Reaction notes

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