Sodium Hydroxide → 2-(3-(4-Cyanophenyl)pyridin-4-ylthio)-2-methylpropanoic acid

HRID 45773Notes

Reaction equation

HRID 45773 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[S:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19]CC)=[O:18])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[S:15][C:16]([CH3:23])([CH3:22])[C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67997194Propanoic acid, 2-[[3-(4-cyanophenyl)-4-pyridinyl]thio]-2-methyl-, ethyl ester

Product 1

HCID 547672282-(3-(4-Cyanophenyl)pyridin-4-ylthio)-2-methylpropanoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To ethyl 2-(3-(4-cyanophenyl)pyridin-4-ylthio)-2-methylpropanoate (step C, 49 mg, 0.15 mmol) was added methanol (0.8 mL), and sodium hydroxide (2 M aqueous, 0.8 mL). The resulting mixture was stirred at ambient temperature for 2 hours. The volume was reduced (˜0.8 mL) by rotary evaporation. To the residue was added HCl (6 N aqueous) with stirring until pH reached 6, resulting in the formation of a white precipitate, which was isolated by filtration. The solid was washed with water (6×1 mL), air dried for 1 hour and dried under vacuum (P2O5) overnight to yield a white powder (28 mg, 64%).

Workup

  1. customby rotary evaporation
  2. additionTo the residue was added HCl (6 N aqueous)
  3. stirringwith stirring until pH
  4. customresulting in the formation of a white precipitate
  5. customwhich was isolated by filtration
  6. washThe solid was washed with water (6×1 mL), air
  7. customdried for 1 hour
  8. dry with materialdried under vacuum (P2O5) overnight

Sources & evidence

ORD record
ord-da2110ddff1144939fb7ead4a777b038
Source dataset
uspto-grants-2013_09
Patent number
US08541589B2

Reaction notes

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