Benzyl Alcohol → Benzyl L-alaninate hydrochloride

HRID 570091Notes

Reaction equation

HRID 570091 reaction equation
[NH2:1][CH:2]([CH3:6])[C:3]([OH:5])=[O:4].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10](S(O)(=O)=O)=[CH:9][CH:8]=1.C(O)C1C=CC=CC=1.O>C1(C)C=CC=CC=1.ClCCl>[CH2:17]([O:4][C:3](=[O:5])[CH:2]([NH2:1])[CH3:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 602DL-alanineHCID 962WaterHCID 6101p-Toluenesulfonic acid

Product 1

HCID 437645Benzyl L-alaninate hydrochloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

4.45 g (50 mMol) 2-Amino propanoic acid were added to 9.7 (51 mMol) p-toluenesulphonic acid and 20 ml (193 mMol) Benzyl alcohol in 10 ml toluene. The reaction mixture was heated under reflux for 2 h using a water separator. 30 ml dichloromethane was added to the cooled reaction mixture. The product was purified by flash chromatography using CH2Cl2:CH3OH 50:1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-8c2baf8548a74328ab6f7ea8b7eec033
Source dataset
uspto-grants-2015_05
Patent number
US09023656B2

Reaction notes

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