Triethylamine → HCID 86741788, compound

HRID 2309297Notes

Reaction equation

HRID 2309297 reaction equation
[CH3:1][C@H:2]([CH2:31][CH2:32][CH2:33][C@H:34]([CH3:46])[CH2:35][CH2:36][CH2:37][C@H:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH2:3][CH2:4][O:5][C@H:6]([CH2:9][O:10][CH2:11][CH2:12][C@H:13]([CH3:30])[CH2:14][CH2:15][CH2:16][C@H:17]([CH3:29])[CH2:18][CH2:19][CH2:20][C@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:7]O.[CH2:47]([N:49]([CH2:52]C)[CH2:50]C)C.Cl[P:55]1(=[O:60])[O:59][CH2:58][CH2:57][O:56]1>C1(C)C=CC=CC=1>[OH-:5].[CH3:1][C@H:2]([CH2:31][CH2:32][CH2:33][C@H:34]([CH3:46])[CH2:35][CH2:36][CH2:37][C@H:38]([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]([CH3:43])[CH3:44])[CH2:3][CH2:4][O:5][C@@H:6]([CH2:9][O:10][CH2:11][CH2:12][C@H:13]([CH3:30])[CH2:14][CH2:15][CH2:16][C@H:17]([CH3:29])[CH2:18][CH2:19][CH2:20][C@H:21]([CH3:28])[CH2:22][CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[CH2:7][P:55]([OH:56])([O:59][CH2:58][CH2:57][N+:49]([CH3:52])([CH3:50])[CH3:47])=[O:60]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 810872-Chloro-1,3,2-dioxaphospholane 2-oxideHCID 53932567HCID 53932567, compound

Product 1

HCID 86741788HCID 86741788, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1 mmol of (s)-2,3-bis[[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyl]oxy]propanol was dissolved in 7.5 ml of toluene and the solution was treated with 1.5 mmol of triethylamine and at 0° C. in the course of 30 minutes with 1.5 mmol of 2-chloro-1,3,2-dioxaphospholan-2-oxide in 2 ml of toluene. The reaction mixture was stirred at room temperature for a further 5 hours, the precipitated hydrochloride was filtered off with the exclusion of moisture and the filtrate was evaporated under reduced pressure. The residue was treated with 7.5 ml of a solution of 4 g of trimethylamine in 100 ml of acetonitrile and reacted at 70° C. overnight in a pressure flask, whereby the product precipitated partially. The solvent was removed under reduced pressure, the residue was dissolved in methanol and passed several times over 20 g of ion exchanger Amberlite MB-3. The solvent was removed and the crude product was chromatographed on silica gel with chloroform/methanol water (60:35:5). There was obtained O-[[(S)-2,3-bis[[(3R,7R,11R)-3,7,11,15-tetramethylhexadecyl]oxy]propyl]hydroxyphosphinyl]choline hydroxide (internal salt) in a yield of 76.6%.

Workup

  1. filtrationthe precipitated hydrochloride was filtered off with the exclusion of moisture
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe residue was treated with 7.5 ml of a solution of 4 g of trimethylamine in 100 ml of acetonitrile
  4. customreacted at 70° C. overnight in a pressure flask
  5. customwhereby the product precipitated partially
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in methanol
  8. customThe solvent was removed
  9. customthe crude product was chromatographed on silica gel with chloroform/methanol water (60:35:5)

Sources & evidence

ORD record
ord-706a45ef826649abb8202a47378cf1c6
Source dataset
uspto-grants-1987_09
Patent number
US04694084

Reaction notes

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