Water → HCID 86631516, compound

HRID 911883Notes

Reaction equation

HRID 911883 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 NH4Cl. 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-712c73bb6b7f4ef08c759a6fe8fda5ff
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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