Sodium Hydroxide → {2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acid

HRID 914283Notes

Reaction equation

HRID 914283 reaction equation
[C:1]([O:5][C:6](=[O:22])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([O:19]CC)=[O:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6](=[O:22])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([OH:19])=[O:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59758864HCID 59758864, compound

Product 1

HCID 59759443{2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-1,3-thiazol-4-yl}acetic acidYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-{[4-(2-Ethoxy-2-oxoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (150 g) synthesized in Example 2 was dissolved in methanol (700 mL), a 1N aqueous sodium hydroxide solution (448 mL) was added at room temperature, and the mixture was stirred for 3 hr. The reaction solution was concentrated under reduced pressure, an aqueous 10% citric acid solution (1 L) was added, and the mixture was extracted with ethyl acetate (1 L). The organic layer was washed three times with water (500 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (123 g) as a slightly yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionan aqueous 10% citric acid solution (1 L) was added
  3. extractionthe mixture was extracted with ethyl acetate (1 L)
  4. washThe organic layer was washed three times with water (500 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b1313fd7d5994ddaaf2954144ac0cd8a
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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