Trimethylamine → HCID 18637148, compound

HRID 329500Notes

Reaction equation

HRID 329500 reaction equation
[P:1]([O-:63])([O:59][CH2:60][CH2:61]Br)([O:3][CH:4]([C@H:32]1[C@H:37]([O:38][C:39](=[O:58])[NH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:36][CH2:35][CH2:34][O:33]1)[C@H]1[C@H](OC(=O)NCCCCCCCCCCCCCCCCC)CCCO1)=[O:2].[CH3:64][N:65]([CH3:67])[CH3:66]>C(Cl)(Cl)Cl.C(O)(C)C.CN(C)C=O.C(=O)([O-])[O-].[Ag+2]>[P:1]([O-:63])([O:59][CH2:60][CH2:61][N+:65]([CH3:67])([CH3:66])[CH3:64])([O:3][CH2:4][C@H:32]1[C@H:37]([O:38][C:39](=[O:58])[NH:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:36][CH2:35][CH2:34][O:33]1)=[O:2]

Participants

7

Reactant 2

HCID 1146TrimethylamineHCID 131716227HCID 131716227, compound

Product 1

HCID 18637148HCID 18637148, compound

Reagents, catalysts & solvents 4

HCID 178418647HCID 178418647, compoundCatalystHCID 3776IsopropanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1.402 g of dl-[trans-3-(N-heptadecylcarbamoyloxy)tetrahydropyran-2-yl]methyl 2-bromoethyl phosphate (prepared as described in Example 1f) was dissolved in a 3:5:5 by volume mixture of chloroform, isopropanol and dimethylformamide, and 7.0 g of gaseous trimethylamine were introduced into the solution. The mixture was heated, under a nitrogen atmosphere, on an oil bath kept at 50° for 6 hours, whilst stirring, and was then cooled, after which 0.483 g of silver carbonate was added The mixture was heated under reflux for 1 hour, and then the solvent was distilled off. Methanol was added to the residue and insolubles were separated by filtration. The solvent was stripped from the resulting solution by evaporation under reduced pressure. The residue was purified by liquid chromatography [using 30 g of silica gel and a Lobar column (size B)], giving 0.930 g of the title compound as a white powder from the fractions eluted with a 32:7:1 by volume mixture of methylene chloride, methanol and water.

Workup

  1. additionwere introduced into the solution
  2. temperatureThe mixture was heated, under a nitrogen atmosphere, on an oil bath
  3. temperaturewas then cooled
  4. temperaturewas heated
  5. temperatureunder reflux for 1 hour
  6. distillationthe solvent was distilled off
  7. additionMethanol was added to the residue and insolubles
  8. customwere separated by filtration
  9. customThe solvent was stripped from the resulting solution by evaporation under reduced pressure
  10. customThe residue was purified by liquid chromatography [

Sources & evidence

ORD record
ord-696f47e336924b548e5bb0e843255016
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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