Aminoisobutyric acid → HCID 18365440, compound

HRID 380588Notes

Reaction equation

HRID 380588 reaction equation
[NH2:1][C:2]([CH3:7])([CH3:6])[C:3]([OH:5])=[O:4].[N:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[S:18][C:17]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][CH:15]=1>[OH-].[Na+].O1CCOCC1>[CH3:6][C:2]([NH:1][S:19]([C:17]1[S:18][C:14]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]=2)=[CH:15][CH:16]=1)(=[O:20])=[O:21])([CH3:7])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 2

HCID 6119Aminoisobutyric acidHCID 27372315-(2-Pyridyl)thiophene-2-sulfonyl chloride

Product 1

HCID 18365440HCID 18365440, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-2-methylpropionic acid (2.0 grams, 19.4 mmole) in 1 N aqueous sodium hydroxide solution (45 mL) and dioxane (45 mL) was added 5-pyridin-2-ylthiophene-2-sulfonyl chloride (8.41 grams, 32.4 mmole). The resulting mixture was stirred at room temperature for 16 hours. Additional 1 N aqueous sodium hydroxide solution (45 mL) was added to the reaction mixture which was then extracted with diethyl ether. The organic extracts were discarded. The aqueous layer was acidified with 1 N hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate fractions were washed with brine, dried over magnesium sulfate and concentrated to afford 2-methyl-2-(5pyridin-2-ylthiophene-2-sulfonylamino)propionic acid as a white solid (2.18 grams, 34%).

Workup

  1. extractionwas then extracted with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate fractions were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5a0204015edb429aa9727c3af8b4dfc7
Source dataset
uspto-grants-2001_10
Patent number
US06303636B1

Reaction notes

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