Sodium hydride → HCID 86743244, compound

HRID 231947Notes

Reaction equation

HRID 231947 reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[H-].[Na+].[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C@@H:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23]O)(=[O:20])=[O:19])=[CH:14][CH:13]=1>O1CCCC1>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C@@H:22]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:23][P:1](=[O:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3780918DiethylphosphiteHCID 44575064HCID 44575064, compound

Product 1

HCID 86743244HCID 86743244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl phosphite (8.9 ml., 69 mmole) is dissolved in dry tetrahydrofuran (125 ml.) under argon in a 250 ml. round-bottomed flask equipped with a condenser. Sodium hydride (2.4 g.) is added in small portions with frothing and bubbling. When the evolution of hydrogen ceases, the reaction mixture is heated to reflux for 45 minutes. It is then cooled to room temperature, and a solution of (S)-2-[[(4-methylphenyl)sulfonyl]amino]-1-hexanol, 4-methylbenzenesulfonate ester (18.1 mmole) is added dropwise over 5 minutes. A white solid precipitates. The mixture is then heated to reflux for 3.5 hours. It is cooled and partitioned between ethyl acetate and 5% potassium bisulfate. The ethyl acetate layer is washed with 5% potassium bisulfate, saturated sodium bicarbonate, and brine, and then concentrated in vacuo. The resulting gum is triturated with hexane to give 6.45 g. of beige solid (S)-[2-[[(4-methylphenl)sulfonyl]amino]hexyl]phosphonic acid, diethyl ester.

Workup

  1. customround-bottomed flask equipped with a condenser
  2. custombubbling
  3. temperatureWhen the evolution of hydrogen ceases, the reaction mixture is heated
  4. temperatureto reflux for 45 minutes
  5. customA white solid precipitates
  6. temperatureThe mixture is then heated
  7. temperatureto reflux for 3.5 hours
  8. temperatureIt is cooled
  9. custompartitioned between ethyl acetate and 5% potassium bisulfate
  10. washThe ethyl acetate layer is washed with 5% potassium bisulfate, saturated sodium bicarbonate, and brine
  11. concentrationconcentrated in vacuo
  12. customThe resulting gum is triturated with hexane
  13. customto give 6.45 g

Sources & evidence

ORD record
ord-0e95c12e968340baa999494f709e916f
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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