Sodium Hydroxide → HCID 69672723, compound

HRID 705362Notes

Reaction equation

HRID 705362 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10](S(C)(=O)=O)[S:11]([CH3:14])(=[O:13])=[O:12])[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[NH:10][S:11]([CH3:14])(=[O:12])=[O:13])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69673091HCID 69673091, compound

Product 1

HCID 69672723HCID 69672723, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of Example 17E (1.85 g, 6.37 mmol) in tetrahydrofuran (32 mL) was treated with sodium hydroxide solution (1.0 N, 16 mL, 16 mmol) and then stirred at room temperature for 1 hour. The mixture was concentrated in vacuo to remove the tetrahydrofuran and the mixture was diluted with water and cooled to 0° C. The solution was acidified to pH 7 by addition of 1 N aqueous hydrochloric acid solution. The mixture was extracted with dichloromethane (2×) and the combined extracts were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. These procedures afforded the product (1.14 g, 84%) as a light beige solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove the tetrahydrofuran
  3. additionthe mixture was diluted with water
  4. temperaturecooled to 0° C
  5. additionThe solution was acidified to pH 7 by addition of 1 N aqueous hydrochloric acid solution
  6. extractionThe mixture was extracted with dichloromethane (2×)
  7. dry with materialthe combined extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-7892b0d6795d4930a031f675b54679aa
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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