Water → HCID 86631516, compound

HRID 335204Notes

Reaction equation

HRID 335204 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[N:13]=2)=[N:6][CH:7]=1.O.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[N:13]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86631517HCID 86631517, compound

Product 1

HCID 86631516HCID 86631516, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 3-(2-(5-bromo-3-(phenylthio)pyridin-2-ylamino)thiazol-4-yl)propanoate (1.40 g, 3.11 mmol) in 50 mL THF was added 25 mL water followed by sodium hydroxide (0.249 g, 6.22 mmol) and the mixture was stirred overnight. The mixture was concentrated to dryness, water added and acidified with NH4C1. The mixture was then extracted with THF. The organics were dried over Na2SO4 and concentrated to give the title compound (1.38 g, 102% yield) that was used as the crude material.

Workup

  1. concentrationThe mixture was concentrated to dryness, water
  2. additionadded
  3. extractionThe mixture was then extracted with THF
  4. dry with materialThe organics were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b61cca398f3946878d5464052bc0ef4b
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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