Potassium Iodide → N-(2-methylphenyl)valine

HRID 648247Notes

Reaction equation

HRID 648247 reaction equation
Br[CH:2]([CH:20]([CH3:22])[CH3:21])[C:3]([O:5]CC1C=CC=C(OC2C=CC=CC=2)C=1)=[O:4].[CH3:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].[I-].[K+]>S(=O)(=O)(O)O>[CH3:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH:26][C@H:2]([C:3]([OH:5])=[O:4])[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 7242O-ToluidineHCID 13229492m-Phenoxybenzyl alpha-bromoisovalerate

Product 1

HCID 53935959N-(2-methylphenyl)valine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To m-phenoxybenzyl α-bromoisovalerate (2 g, 0.0055 mole), 24°, is added 2-methylaniline (2.95 g, 0.0275 mole) followed by a catalytic amount of potassium iodide (20 mg). The reaction mixture is heated, 110°-115°, for about 36 hours, and then poured into ice-water (30 ml) and 2 N sulfuric acid (10 ml) and extracted with ether (3×30 ml). The combined ether extracts are washed with water (2×30 ml) until neutral and with brine (10 ml) followed by drying over calcium sulfate. The reaction product is concentrated under vacuum and isolated by preparative TLC to yield 3-phenoxybenzyl ester of N-(2-methylphenyl)valine. MS m/e 389.2 (M+).

Workup

  1. temperatureThe reaction mixture is heated, 110°-115°, for about 36 hours
  2. extractionextracted with ether (3×30 ml)
  3. washThe combined ether extracts are washed with water (2×30 ml) until neutral and with brine (10 ml)
  4. dry with materialby drying over calcium sulfate
  5. concentrationThe reaction product is concentrated under vacuum
  6. customisolated by preparative TLC

Sources & evidence

ORD record
ord-1001254eff5749d68b81cbe7333d1fa5
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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