Hydrochloric Acid → N-Tosyl-L-alanine

HRID 1289353Notes

Reaction equation

HRID 1289353 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].Cl>C1(C)C=CC=CC=1.[OH-].[Na+]>[S:7]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 737622N-Tosyl-L-alanine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

100 g of p-toluene sulfonyl chloride in 200 ml of toluene was slowly added to 50 g (0.505 mole) of L-alanine dissolved in 1 l 1N-sodium hydroxide cooled to below 5° C. and stirred at room temperature for 24 hours. Then, the aquose layer was cooled to below 5° C. and with a slow addition of concentrated hydrochloric acid, pH was adjusted to 1.5. After standing in the refrigerator for 3 to 4 hours, the white solid, so formed,.was filtered, washed with water sufficiently and dried.

Workup

  1. temperaturecooled to below 5° C.
  2. waitAfter standing in the refrigerator for 3 to 4 hours
  3. filtrationthe white solid, so formed,.was filtered
  4. washwashed with water sufficiently
  5. customdried

Sources & evidence

ORD record
ord-fe596eaa8e3b45ab813131429170de41
Source dataset
uspto-grants-1998_05
Patent number
US05750359

Reaction notes

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