Benzyl Alcohol → L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

HRID 614765Notes

Reaction equation

HRID 614765 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[NH2:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18].[CH2:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[CH2:23]([O:21][C:20](=[O:22])[C@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH2:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 6106L-LeucineHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)Yield 94%

Procedure

In a 200 ml 3 neck flask equipped with a Dean and Stark trap, reflux condenser (with drying tube attached), and mechanical stirrer, 15 grams (0.0789 mole) of p-toluenesulfonic acid monohydrate is refluxed until one equivalent of water is released. At this point 10 grams (0.07634 mole) leucine and 17.0 grams (0.15 mole) benzyl alcohol are added. The mixture is refluxed for 4 hours and allowed to cool to room temperature. The solvents are removed in vacuo and a white, solid residue is produced. The white solid is washed with anhydrous ether and recrystallized from ethanol/ether to yield in three crops 28.2 grams of leucine benzyl ester p-toluene sulfonate (94% yield) having a melting point of 157°-158° C. (with decomposition).

Workup

  1. temperaturereflux condenser
  2. temperatureThe mixture is refluxed for 4 hours
  3. customThe solvents are removed in vacuo
  4. customa white, solid residue is produced
  5. washThe white solid is washed with anhydrous ether
  6. customrecrystallized from ethanol/ether

Sources & evidence

ORD record
ord-bdd56fc1508948f999d85f74d6a8c766
Source dataset
uspto-grants-1979_03
Patent number
US04146614

Reaction notes

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