L-Alanine → N-Tosyl-L-alanine

HRID 246876Notes

Reaction equation

HRID 246876 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1>[OH-].[Na+].C1(C)C=CC=CC=1>[S:13]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 5950L-AlanineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 737622N-Tosyl-L-alanine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
5 °C

Procedure

L-alanine (100 g; 1.11 moles) was dissolved in 2.25 L of 1N sodium hydroxide (aq), cooled to 5° C. and stirred while a solution of p-toluenesulfonyl chloride (218 g; 1.11 moles) in 450 mL of toluene was added slowly. The mixture was stirred at ambient temperature for 20 hr. The layers were separated and the chilled aqueous layer acidified to pH 1 with concentrated hydrochloric acid. The white solid title compound was collected by filtration, washed with water and dried. Yield 178.5 g (66%) mp 134°-5° C. IR (CHCl3) cm-1 1726, 1340, 1165, 1095; 1H NMR (DMSO-D6) δ 1.20 (d, J=7, 3H), 2.40 (s, 3H), 3.85 (p, J=8, 1H), 6.4 (br d, 1H)(CO2H), 7.41 (d, JAB =8, 2H) and 7.75 (d, JAB =8, 2H) [center of pattern: 7.58; ΔVAB =20.49 Hz], 8.03 (br d, J=8, 1H)(NH).

Workup

  1. additionwas added slowly
  2. customThe layers were separated
  3. filtrationThe white solid title compound was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-df2e61c0c3694d17b0ed9eb90a1fd0d2
Source dataset
uspto-grants-1987_11
Patent number
US04704460

Reaction notes

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