Sodium Hydroxide → HCID 117830978, compound

HRID 515879Notes

Reaction equation

HRID 515879 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CC1C=CC(S(O[CH2:18][C@@H:19]2[CH2:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:21][N:20]2[S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])(=O)=O)=CC=1.[OH-].[Na+]>C(OC)(C)(C)C>[CH3:18][C@@H:19]1[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][N:20]1[S:29]([C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117830854HCID 117830854, compound

Product 1

HCID 117830978HCID 117830978, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 8.15 g (214.8 mmol) of lithium aluminium hydride (LiAlH4) in 800 mL of methyl tert-butyl ether (MTBE) there are added 101.2 g of the ditosyl compound obtained in Step A (214.8 mmol) dissolved in 200 mL of MTBE. The batch is then heated at 50° C. for 2 hours. It is allowed to cool and placed at 0° C., and there are then added, dropwise, 12 mL of 5N NaOH solution. The batch is stirred at ambient temperature for 45 minutes. The solid thereby obtained is then filtered off and washed with MTBE and then with dichloromethane. The filtrate is then concentrated to dryness. The title product is then obtained in the form of a solid.

Workup

  1. temperatureto cool
  2. customplaced at 0° C.
  3. additionthere are then added
  4. customThe solid thereby obtained
  5. filtrationis then filtered off
  6. washwashed with MTBE
  7. concentrationThe filtrate is then concentrated to dryness

Sources & evidence

ORD record
ord-3221fd17c5e44505bf3678f8a8deea4f
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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