Benzyl Alcohol → (S)-N-Methylalanine benzyl ester p-toluene sulfonic acid salt

HRID 54500Notes

Reaction equation

HRID 54500 reaction equation
[CH3:1][NH:2][C@H:3]([C:5]([OH:7])=[O:6])[CH3:4].[CH2:8](O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.O>C1(C)C=CC=CC=1.CCOCC>[C:17]1([CH3:27])[CH:18]=[CH:19][C:20]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:21][CH:22]=1.[CH2:8]([O:6][C:5](=[O:7])[C@H:3]([CH3:4])[NH:2][CH3:1])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 5288725N-Methyl-L-Alanine

Product 1

HCID 86749482(S)-N-Methylalanine benzyl ester p-toluene sulfonic acid salt

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1.55 g (15.0 mmol) of (S)-N-methylalanine and 9.31 (90.0 mmol) of benzyl alcohol in 30 mL of toluene was treated with 3.00 g (15.8 mmol) of p-toluenesulfonic acid monohydrate. The mixture was heated for 19 hours under reflux with removal of water via a Dean-Stark trap. After cooling, the reaction solution was poured into 200 mL of ether, precipitating a yellow oil. The solvents were decanted and the residue was taken up into ethyl acetate and concentrated to yield a viscous, light yellow oil (22); TLC: Rf =0.34, 95:5:0.5 CH2Cl2 /MeOH/concentrated ammonium hydroxide; 1H NMR (300 MHz) consistent with structure.

Workup

  1. temperatureThe mixture was heated for 19 hours
  2. temperatureAfter cooling
  3. customprecipitating a yellow oil
  4. customThe solvents were decanted
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af38bc6f662a4fc3bb383e05d4742834
Source dataset
uspto-grants-1997_04
Patent number
US05622970

Reaction notes

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