تفاعل #1447086

ord-5626f63031f94706af168d5c2b0968a9

معادلة التفاعل

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
المردود 83.7%
Cc1ccc(S(=O)(=O)O)cc1.N[C@H](CCc1ccccc1)C(=O)OCc1ccccc1
D-Homophenylalanine Benzyl ester Tosylate
المردود 83.7%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةat 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
    أخرىThe residue was triturated with diethyl ether
  4. 4
    ترشيحthe solid was filtered
  5. 5
    أخرىdried

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07879795B2uspto-grants-2011_02