Реакция #1447086

ord-5626f63031f94706af168d5c2b0968a9

Уравнение реакции

Cl.N[C@H](CCc1ccccc1)C(=O)O
D-Homophenylalanine hydrochloride
OCc1ccccc1
benzyl alcohol
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
Cc1ccc(S(=O)(=O)O)cc1.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1
title product
Выход 83.7%
Cc1ccc(S(=O)(=O)O)cc1.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1
D-Homophenylalanine Benzyl ester Tosylate
Выход 83.7%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Температураat reflux in Dean Stark apparatus during 5 hrs
  2. 2
    workup.DISTILLATIONafter which time additional benzene (100 mL) was distilled from reaction mixture
  3. 3
    ДругоеThe residue was triturated with diethyl ether
  4. 4
    Фильтрацияthe solid was filtered
  5. 5
    Другоеdried

Методика

A solution of D-Homophenylalanine hydrochloride (1.7 g, 7.93 mmol), benzyl alcohol (7.2 mL, 64.0 mmol) and p-toluenesulfonic acid monohydrate (1.8 g, 9.5 mmol) in benzene (30 mL) was heated at reflux in Dean Stark apparatus during 5 hrs, after which time additional benzene (100 mL) was distilled from reaction mixture. The residue was triturated with diethyl ether, the solid was filtered and dried to give title product (2.93 g).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07879795B2uspto-grants-2011_02