Palmitoyl chloride → HCID 19891737, compound

HRID 893254Notes

Reaction equation

HRID 893254 reaction equation
[NH2:1][CH:2]([CH:7]([OH:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[C:31](Cl)(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]>C1C=CC=CC=1>[C:31]([NH:1][CH:2]([CH:7]([OH:23])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:3]([O:5][CH3:6])=[O:4])(=[O:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 19891733HCID 19891733, compound

Product 1

HCID 19891737HCID 19891737, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

10.7 g (0.033 mole) of methyl 2-amino-3-hydoxyoctadecanoate prepared according to Example 1 are dissolved in 200 cm3 of dry benzene and then 3.28 g of triethylamine are added. 8.92 g (0.033 mole) of palmitoyl chloride dissolved in 60 cm3 of benzene are added dropwise to this solution between 20 and 35° C. After 3 hours' stirring, the triethylamine hydrochloride is removed by filtration at 40° C. The organic phase is washed twice with 100 cm3 of water. The benzene solution is dried over sodium sulphate and then part of the benzene is removed by evaporation. 16.3 g of methyl 2-hexadecanoylamino-3-hydroxyoctadecanoate are isolated by crystallization.

Workup

  1. additionare added dropwise to this solution between 20 and 35° C
  2. customthe triethylamine hydrochloride is removed by filtration at 40° C
  3. washThe organic phase is washed twice with 100 cm3 of water
  4. dry with materialThe benzene solution is dried over sodium sulphate
  5. custompart of the benzene is removed by evaporation

Sources & evidence

ORD record
ord-cfebaeb94ef44644ac26f6eef92e58fc
Source dataset
uspto-grants-1992_06
Patent number
US05124081

Reaction notes

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