delta-Gluconolactone → dodecyl L-alaninate

HRID 54896

Reaction equation

HRID 54896 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:41])[CH:38]([CH3:40])[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][C@H: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:41])[CH3:40]

Participants

5

Reactant 3

HCID 7027delta-GluconolactoneHCID 8471TriethylamineHCID 86750759DL-alanine dodecyl ester p-toluenesulfonate salt

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 p-toluenesulfonate 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-b5b27c82d27345e5bd0e07644a09240f
Source dataset
uspto-grants-1997_04
Patent number
US05624906

Linked notes

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