Water → HCID 54315219, compound

HRID 1788901Notes

Reaction equation

HRID 1788901 reaction equation
O=[CH:2][C@H:3]([C@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[OH2:11].[CH2:12]([NH2:24])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(O)(C)C>[CH:9]1([N:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])[C:12](=[O:11])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:10][CH2:2][C@@H:3]([OH:4])[C@H:5]([OH:6])[C@@H:7]1[OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 13583DodecylamineHCID 65550Lyxose

Product 1

HCID 54315219HCID 54315219, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10 g of D-lyxose are dissolved in 120 ml of isopropanol and 60 ml of water and the solution is warmed to 70° C. 18 g of dodecylamine are added. After a clear solution has formed, the temperature is maintained for a further 15 minutes. The mixture is cooled to room temperature and evaporated in vacuo. 10 g of the resulting syrup are dissolved in 100 ml of tetrahydrofuran and 10 ml of methanol, and 10 g of sodium carbonate are added. 5.5 g of dodecanoic acid chloride, dissolved in 20 ml of tetrahydrofuran, are added dropwise at 0° C. When the reaction has ended, the mixture is worked up, and the product purified, as described in Example 2.

Workup

  1. customAfter a clear solution has formed
  2. temperaturethe temperature is maintained for a further 15 minutes
  3. customevaporated in vacuo
  4. dissolution10 g of the resulting syrup are dissolved in 100 ml of tetrahydrofuran
  5. addition10 ml of methanol, and 10 g of sodium carbonate are added
  6. dissolution5.5 g of dodecanoic acid chloride, dissolved in 20 ml of tetrahydrofuran
  7. additionare added dropwise at 0° C
  8. customthe product purified

Sources & evidence

ORD record
ord-e81b667d9aad48d78623dcbfce1d50b3
Source dataset
uspto-grants-1987_08
Patent number
US04686208

Reaction notes

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