Water → HCID 11991560, compound

HRID 385884Notes

Reaction equation

HRID 385884 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][N:14]([CH2:25][C@H:26]([OH:28])[CH3:27])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=O)=O)=CC=1.[H-].[Na+].O>C1COCC1>[CH3:27][C@H:26]1[O:28][CH2:12][CH2:13][N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH2:25]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 59526126HCID 59526126, compound

Product 1

HCID 11991560HCID 11991560, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[(2R)-2-hydroxypropyl][(4-methylphenyl)sulfonyl]amino}ethyl 4-methylbenzenesulfonate (340 g, 0.80 mol) in dry THF (3 L) at 0° C. was added NaH (60%, 120 g, 3.00 mol) portion wise. The reaction mixture was warmed to room temperature and stirred for 14 h. The reaction was then cooled to 0° C., and water (100 mL) was added to quench the reaction. The mixture was completely quenched by pouring into water (1 L) and the phases were separated. The aqueous phase was extracted with EtOAc (3×500 mL) and the combined organic layers were washed with brine (500 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (8:1 petroleum ether:EtOAc) to yield the title compound as an oil.

Workup

  1. temperatureThe reaction was then cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. customThe mixture was completely quenched
  5. additionby pouring into water (1 L)
  6. customthe phases were separated
  7. extractionThe aqueous phase was extracted with EtOAc (3×500 mL)
  8. washthe combined organic layers were washed with brine (500 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe crude residue was purified by silica gel chromatography (8:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-74d7ad1db3ed439483b932a42b721541
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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