Sulfuric Acid → N-(p-chlorophenyl)valine

HRID 1389336Notes

Reaction equation

HRID 1389336 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].[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.[I-].[K+].S(=O)(=O)(O)O>CN(P(N(C)C)(N(C)C)=O)C>[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C@H:2]([C:3]([OH:5])=[O:4])[CH:20]([CH3:22])[CH3:21])=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 78124-ChloroanilineHCID 13229492m-Phenoxybenzyl alpha-bromoisovalerate

Product 1

HCID 13796078N-(p-chlorophenyl)valine

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

To m-phenoxybenzyl α-bromoisovalerate (5 g, 0.0138 mole) in 9 ml of HMPT, at 24°, is added p-chloroaniline (5.27 g, 0.0413 mole) and a catalytic amount of potassium iodide (60 mg). The reaction mixture is stirred at 70° for four days. The reaction is then poured into ice-water (30 ml) and 10 ml of 2 N sulfuric acid which is extracted with ether (3×30 ml). The combined ether extracts are washed with water (2×30 ml) and brine (10 ml), dried over calcium sulfate, filtered and evaporated. The crude product is purified by preparative TLC to yield the m-phenoxybenzyl ester of N-(p-chlorophenyl)valine.

Workup

  1. extractionis extracted with ether (3×30 ml)
  2. washThe combined ether extracts are washed with water (2×30 ml) and brine (10 ml)
  3. dry with materialdried over calcium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by preparative TLC

Sources & evidence

ORD record
ord-b6aca6868d6f4ef08cc07b1360191f4f
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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