Sodium hydride → HCID 86678256, compound

HRID 1504745Notes

Reaction equation

HRID 1504745 reaction equation
[CH2:1]([O:19][P:20]([C:41](=[CH2:52])[CH2:42][CH2:43][CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[S].[H-].[Na+]>[P].C1COCC1>[CH2:1]([O:19][P:20]([CH:41]([CH2:52][CH2:41][P:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:21])[CH2:42][CH2:43][CH2:44][C:45]([O:47][C:48]([CH3:50])([CH3:49])[CH3:51])=[O:46])([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 5362487SulfurHCID 86678257HCID 86678257, compound2×

Product 1

HCID 86678256HCID 86678256, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 5462309PhosphorusSolvent

Procedure

Dioctadecyl hydrogen phosphonate may be reacted with tert-butyl 5-(bis(octadecyloxy)phosphoryl)hex-5-enoate, D, prepared in Example 4 using substantially the conditions found in Phosphorus, Sulfur and Silicon and the Related Elements, 83 (1-4), 77-98:1993 and outlined in FIG. 6. Thus, dioctadecyl hydrogen phosphonate (MW 586.95, 1.56 g, 2.66 mmol), dissolved in THF (30 mL) and sodium hydride (95%, FW 24.0, 2.66 mmol, 0.064 g) are allowed to react under inert atmosphere at RT with stirring. Then tert-butyl 5-(bis(octadecyloxy)phosphoryl)hex-5-enoate (MW 1356.2, 3.65 g, 2.69 mmol) in THF is added and allowed to react under an inert atmosphere until the reaction is complete. The reaction progress may be followed by TLC, rphplc or 31P nmr. At the completion of reaction the solvent may be removed by evaporation and the crude product purified by normal phase flash chromatography using a suitable solvent system (e.g., hexanes-ethyl acetate gradient (ELSD detection) to yield substantially pure product. The crude product may also be purified using reverse phase HPLC (e.g., C4, 300 A, and a suitable solvent gradient, e.g., water;isopropanol). The MS of the desired product is M+H+ 1357.2, M+Na+ 1379.2.

Workup

  1. customprepared in Example 4 using substantially the conditions
  2. customto react under inert atmosphere at RT
  3. customto react under an inert atmosphere until the reaction
  4. customAt the completion of reaction the solvent
  5. custommay be removed by evaporation
  6. customthe crude product purified by normal phase flash chromatography
  7. customto yield substantially pure product
  8. customThe crude product may also be purified

Sources & evidence

ORD record
ord-07b18d6cbe304fdc8967464624636c50
Source dataset
uspto-grants-2015_12
Patent number
US09216225B2

Reaction notes

Loading…