تفاعل #528294

ord-34768e3da1ca474e9bfb828947fbbbcc

معادلة التفاعل

O=C1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
D-glucono-1,5-lactone
CCCCCCCCCCCCOC(=O)CN.Cc1ccc(S(=O)(=O)O)cc1
glycine dodecyl ester p-toluenesulfonate salt
CCN(CC)CC
triethylamine
CCCCCCCCCCCCOC(=O)CN
dodecyl glycinate
المردود 61.0%

المذيبات

ظروف التفاعل

درجة الحرارة
50°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىA 100 ml round bottom flask equipped with a condenser, addition funnel
  2. 2
    workup.ADDITIONwere added dropwise over 15 minutes from an addition funnel
  3. 3
    درجة الحرارةcooled to room temperature
  4. 4
    ترشيحThe white product was filtered
  5. 5
    غسيلwashed with chloroform (3×150 ml)
  6. 6
    أخرىdried under high vacuum at 35° C.

الإجراء التجريبي

A 100 ml round bottom flask equipped with a condenser, addition funnel, thermometer and mechanical stirrer was charged with D-glucono-1,5-lactone (5.0 g, 0.03 mole) and isopropanol (35 g). The suspension was heated to 50° C. over 15 minutes. A mixture of glycine dodecyl ester p-toluenesulfonate salt (11.7 g, 0.03 mole), triethylamine (2.9 g 0.03 mole) and isopropanol (20 g) were added dropwise over 15 minutes from an addition funnel. The reaction mixture was stirred rapidly for about 2 hrs and then cooled to room temperature. The white product was filtered, washed with chloroform (3×150 ml) and dried under high vacuum at 35° C. giving 7.2 g (61% yield) of N-D-gluconyl dodecyl glycinate with a melting point of 121°-122° C. and 98.6% purity.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05521293uspto-grants-1996_05