Trimethylamine → HCID 88688023, compound

HRID 1285239Notes

Reaction equation

HRID 1285239 reaction equation
[P:1]([O-:35])([O:31][CH2:32][CH2:33]Br)([O:3][CH2:4][CH:5]([O:29][CH3:30])[CH2:6][O:7][C:8](=[O:28])[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][CH2:26][CH3:27])=[O:2].[CH3:36][N:37]([CH3:39])[CH3:38]>C1(C)C=CC=CC=1>[P:1]([O-:35])([O:31][CH2:32][CH2:33][N+:37]([CH3:39])([CH3:38])[CH3:36])([O:3][CH2:4][CH:5]([O:29][CH3:30])[CH2:6][O:7][C:8](=[O:28])[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][CH2:26][CH3:27])=[O:2]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 131713133HCID 131713133, compound

Product 1

HCID 88688023HCID 88688023, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 60 ml of toluene containing 10 g of trimethylamine is dissolved 2.0 g of the phosphate ester obtained in Example 10, and the solution is allowed to stand at room temperature for 3 days. The reaction mixture is concentrated to dryness under reduced pressure, the residue is dissolved in 50 ml of methanol, and 2 g of silver carbonate is added. The mixture is refluxed for 1 hour and, then, filtered. The filtrate is evaporated to dryness, and the residue 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 640 mg of the contemplated product as colorless powders.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  2. dissolutionthe residue is dissolved in 50 ml of methanol
  3. addition2 g of silver carbonate is added
  4. temperatureThe mixture is refluxed for 1 hour
  5. filtrationfiltered
  6. customThe filtrate is evaporated to dryness
  7. customthe residue 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-e355722b9074442c9c73581122002412
Source dataset
uspto-grants-1986_01
Patent number
US04565865

Reaction notes

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