L-Alanine → N-Tosyl-L-alanine

HRID 1860231Notes

Reaction equation

HRID 1860231 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14]>C1(C)C=CC=CC=1.[OH-].[Na+]>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 5950L-AlanineHCID 73974-Toluenesulfonyl chloride2×

Product 1

HCID 737622N-Tosyl-L-alanine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

50.0 g of p-toluenesulfonyl chloride was added to 100 ml of 90° C. toluene with stirring. The p-toluenesulfonyl chloride solution in toluene was slowly added to 25.0 g of L-alanine dissolved in 500 ml of 1N NaOH cooled to 5° C. and stirred for 24 hours. The resulting aqueous layer is separated and cooled to below 5° C. and with the addition of concentrated hydrochloric acid, pH was adjusted to 1.5. After standing in the refrigerator for 3 to 4 hours, the white solid crystals, so formed, were filtered, twice washed with water, and dried.

Workup

  1. stirringstirred for 24 hours
  2. customThe resulting aqueous layer is separated
  3. temperaturecooled to below 5° C. and with the addition of concentrated hydrochloric acid, pH
  4. customthe white solid crystals, so formed
  5. filtrationwere filtered
  6. washtwice washed with water
  7. customdried

Sources & evidence

ORD record
ord-94ff6740ff344f7eaa18ff3d30360eb5
Source dataset
uspto-grants-2003_03
Patent number
US06528652B1

Reaction notes

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