Trimethylamine → HCID 13560105, compound

HRID 647273Notes

Reaction equation

HRID 647273 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.

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-ae27ba3f8db1403db719d848a3755b6e
Source dataset
uspto-grants-1983_10
Patent number
US04408052

Reaction notes

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