Tetrahydrofuran → 2-(4-Chloro-5-iodo-2-methoxyphenylamino)propanoic acid

HRID 588857Notes

Reaction equation

HRID 588857 reaction equation
[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH:9][CH:10]([CH3:15])[C:11]([O:13]C)=[O:12])=[C:4]([O:16][CH3:17])[CH:3]=1.O1CCCC1.O[Li].O>O>[Cl:1][C:2]1[C:7]([I:8])=[CH:6][C:5]([NH:9][CH:10]([CH3:15])[C:11]([OH:13])=[O:12])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 117610370Methyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)propanoate

Product 1

HCID 1176103722-(4-Chloro-5-iodo-2-methoxyphenylamino)propanoic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-(4-chloro-5-iodo-2-methoxyphenylamino)propanoate (1.12 g, 3.04 mmol) in mixture of tetrahydrofuran (20 mL) and water (10 mL) at RT, LiOH.H2O (0.51 g, 12.16 mmol) was added and the resulting mixture was stirred for 1 h. The aqueous phase was washed with TBME and then acidified with aqueous HCl (1N) to adjust the pH to 5. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford the crude product (760 mg) which was used directly in the next step without further purification. ESI-MS m/z: 356.1[M+H]+.

Workup

  1. washThe aqueous phase was washed with TBME
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b3b71a0508d744b4aeda6e4549eb8dc1
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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