Water → HCID 70003939, compound

HRID 1266706Notes

Reaction equation

HRID 1266706 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH:10]([C:14]2[CH:19]=[C:18]([O:20][CH2:21][CH3:22])[C:17]([O:23][CH2:24][CH2:25][OH:26])=[CH:16][C:15]=2[F:27])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].[CH2:34](I)[CH2:35][CH2:36][CH3:37].O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:34]([O:12][C:11](=[O:13])[CH:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:14]1[CH:19]=[C:18]([O:20][CH2:21][CH3:22])[C:17]([O:23][CH2:24][CH2:25][OH:26])=[CH:16][C:15]=1[F:27])[CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 18551845HCID 18551845, compound

Product 1

HCID 70003939HCID 70003939, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

The (RS)-(4-cyano-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid (226 mg) described in example 1.25 was dissolved in DMF (2 ml). Potassium carbonate (167 mg), n-butyl iodide (556 mg) and tetrabutylammonium iodide (22 mg) were added and the mixture was stirred overnight at r.t. Water was added and the mixture was extracted with EtOAc. The org. phase was washed with water, dried, filtered and concentrated. The product was purified by chromatography (SiO2, EtOAc/hexane) to give 146 mg of (RS)-(4-cyano-phenylamino)-[5-ethoxy-2-fluoro-4-(2-hydroxy-ethoxy)-phenyl]-acetic acid butyl ester as a colorless solid. MS: 453 ([M+Na]+).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washphase was washed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by chromatography (SiO2, EtOAc/hexane)

Sources & evidence

ORD record
ord-db624014374a4273a7fe84585e3c7f71
Source dataset
uspto-grants-2003_04
Patent number
US06548694B2

Reaction notes

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