Trimethylamine → HCID 13560105, compound

HRID 1285237Notes

Reaction equation

HRID 1285237 reaction equation
[P:1]([O-:32])([O:28][CH2:29][CH2:30]Br)([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:27])[NH: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][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:2].[CH3:33][N:34]([CH3:36])[CH3:35]>C1(C)C=CC=CC=1>[P:1]([O-:32])([O:28][CH2:29][CH2:30][N+:34]([CH3:36])([CH3:35])[CH3:33])([O:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:27])[NH: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][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:2]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 20250380HCID 20250380, compound

Product 1

HCID 13560105HCID 13560105, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

The entire amount of the phosphate ester obtained in Example 3 is dissolved in 70 ml of toluene containing 14 g of trimethylamine under anhydrous state and heated at 60° C. for 48 hours. The reaction mixture is concentrated to dryness under reduced pressure, and the residue is dissolved in 40 ml of methanol, vigorously stirred in the presence of 2.7 g of silver carbonate and heated under reflux for 1 hour. After filtration, the filtrate is evaporated to dryness, and the product is separated and purified by silica gel chromatography [eluent: chloroform-methanol-water (65:25:4)] and crystallized from chloroform-acetone. By this procedure is obtained 0.9 g of the above-indicated compound as colorless crystalline powder. ##STR20##

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  2. dissolutionthe residue is dissolved in 40 ml of methanol
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. customthe product is separated
  8. custompurified by silica gel chromatography [eluent: chloroform-methanol-water (65:25:4)]
  9. customcrystallized from chloroform-acetone

Sources & evidence

ORD record
ord-eeb2733155044da7a97bfb493249f78e
Source dataset
uspto-grants-1986_01
Patent number
US04565865

Reaction notes

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