Diethyl Ether → HCID 65661124, compound

HRID 986810Notes

Reaction equation

HRID 986810 reaction equation
[NH2:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3].[C:7]1(C)[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[CH2:18](OCC)C>[OH-].[Na+]>[C:9]1([CH3:18])[C:10]([S:13]([NH:1][C@H:2]([C:4]([OH:6])=[O:5])[CH3:3])(=[O:14])=[O:15])=[CH:11][CH:12]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 5950L-AlanineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 65661124HCID 65661124, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
4 °C

Procedure

0.01 mol of L-alanine were dissolved in 20 ml of 1-molar sodium hydroxide solution, a solution of 0.01 mol of p-toluenesulfonyl chloride in 10 ml of diethyl ether was added, and the mixture was vigorously stirred for 4 h. The ether phase was separated off, and the aqueous phase was acidified to pH 3 with concentrated hydrochloric acid. The crude n-toluenesulfonyl-1-alanine started to crystallize (cooling to 4° C. where necessary) and was filtered off and recrystallized from 60% by volume aqueous alcohol. Melting point 130°-131° C.

Workup

  1. customThe ether phase was separated off
  2. customto crystallize
  3. filtrationwas filtered off
  4. customrecrystallized from 60% by volume aqueous alcohol

Sources & evidence

ORD record
ord-993071511caa44f9938d976c86a46209
Source dataset
uspto-grants-1987_12
Patent number
US04716222

Reaction notes

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