delta-Gluconolactone → Dodecyl glycinate

HRID 2293649

Reaction equation

HRID 2293649 reaction equation
C1(=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24]([O:36][C:37](=[O:40])[CH2:38][NH2:39])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C(N(CC)CC)C>C(O)(C)C>[NH2:39][CH2:38][C:37]([O:36][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:40]

Participants

5

Reactant 3

HCID 7027delta-GluconolactoneHCID 8471TriethylamineHCID 15435490Glycine 1-dodecyl ester tosylate

Product 1

HCID 6452634Dodecyl glycinateYield 61%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
50 °C

Procedure

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.

Workup

  1. customA 100 ml round bottom flask equipped with a condenser, addition funnel
  2. additionwere added dropwise over 15 minutes from an addition funnel
  3. temperaturecooled to room temperature
  4. filtrationThe white product was filtered
  5. washwashed with chloroform (3×150 ml)
  6. customdried under high vacuum at 35° C.

Sources & evidence

ORD record
ord-183163d501c448d8b604ff1cc3542713
Source dataset
uspto-grants-1997_11
Patent number
US05686603

Linked notes

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