Potassium Iodide → HCID 54187330, compound

HRID 1389355Notes

Reaction equation

HRID 1389355 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].Br[CH:13]([CH:17]([CH3:19])[CH3:18])[C:14]([OH:16])=[O:15].[I-].[K+]>CN(P(N(C)C)(N(C)C)=O)C>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C@H:13]([C:14]([OH:16])=[O:15])[CH:17]([CH3:19])[CH3:18])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 112682-Bromoisovaleric acidHCID 663013,5-Dimethoxyaniline

Product 1

HCID 54187330HCID 54187330, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A mixture of 3,5-dimethoxyaniline (2.1 g), the m-phenoxybenzyl ester of α-bromoisovaleric acid (1.0 g), potassium iodide (72.9 mg) and 5 ml of HMPT is heated overnight at 70°-80°. The reaction is then worked up by partition between 100 ml of 2 N sulfuric acid and 100 ml of ether. The aqueous phase is extracted with ether and then the combined ether phases are washed with 2 N sulfuric acid, saturated sodium bicarbonate and brine, dried over potassium carbonate, filtered and evaporated. The residue is subjected to prep. TLC eluting with ether/hexane to yield the m-phenoxybenzyl ester of N-(3,5-dimethoxyphenyl)valine. MS m/e 435.2 (M+, 11.7), 208.1 (100).

Workup

  1. customby partition between 100 ml of 2 N sulfuric acid and 100 ml of ether
  2. extractionThe aqueous phase is extracted with ether
  3. washthe combined ether phases are washed with 2 N sulfuric acid, saturated sodium bicarbonate and brine
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. customevaporated
  7. washTLC eluting with ether/hexane

Sources & evidence

ORD record
ord-8e2e8f6397b248b4b8f2ea165f96b8b6
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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