delta-Gluconolactone → dodecyl L-alaninate

HRID 441113

Reaction equation

HRID 441113 reaction equation
C1(=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O.[CH2:13]([O:25][C:26](=[O:30])[CH:27]([CH3:29])[NH2:28])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(N(CC)CC)C>C(O)(C)C>[NH2:28][C@H:27]([C:26]([O:25][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 7027delta-GluconolactoneHCID 8471TriethylamineHCID 6453806Dodecyl 2-aminopropanoate

Product 1

HCID 181533dodecyl L-alaninateYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °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 (7.0 g, 0.04 mole) and isopropanol (30 g). The suspension was heated to 60° C. over 15 minutes. A mixture of DL-alanine dodecyl ester ptoluenesulfonate salt (16.9 g, 0.04 mole), triethylamine (4.0 g 0.04 mole) and isopropanol (20 g) were added dropwise over 15 minutes from an addition funnel. The reaction mixture was stirred rapidly for about 6 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 12.5 g (73% yield) of N-D-gluconyl dodecyl alaninate with a melting point of 97°-98° C. and 98.8% 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-39ad4ba91e1d458da23483f42f65a133
Source dataset
uspto-grants-1996_05
Patent number
US05521293

Linked notes

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