L-Alanine → N-Tosyl-L-alanine

HRID 542403Notes

Reaction equation

HRID 542403 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) dissolved 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 s, 1H)(CO2), 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-b0c09ae2ca3f41dab3f76c1228b94f31
Source dataset
uspto-grants-1987_04
Patent number
US04657855

Reaction notes

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