Taurine → HCID 10399818, compound

HRID 1767273Notes

Reaction equation

HRID 1767273 reaction equation
[CH3:1][C:2]1([CH3:10])[CH:4]([C:5](Cl)=[O:6])[C:3]1([CH3:9])[CH3:8].[NH2:11][CH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15]>[OH-].[Na+].ClCCl>[CH3:1][C:2]1([CH3:10])[C:3]([CH3:9])([CH3:8])[CH:4]1[C:5]([NH:11][CH2:12][CH2:13][S:14]([OH:17])(=[O:16])=[O:15])=[O:6]

Participants

5

Reactant 2

HCID 1123TaurineHCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride

Product 1

HCID 10399818HCID 10399818, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent3×

Procedure

2,2,3,3-tetramethylcyclopropanecarbonyl taurine (TMC-taurine) is synthesized by adding tetramethylcyclopropanecarbonyl chloride (TMC-chloride) to taurine dissolved in a sodium hydroxide solution, preferably 5–15% NaOH aqueous solution, more preferably 10% NaOH aqueous solution. The reaction mixture is stirred for 3–10 hrs, preferably for 5 hr at room temperature (20–25° C.). The water is evaporated and the product is extracted by boiling ethanol. The insoluble salts are filtered off and TMC-taurine is crystallized using ethanol:diethyl ether solution. TMC-taurine is chlorinated in dry dichloromethane using thionyl chloride and the suitable amides (compound XXVII in reaction scheme II) are synthesized by slowly adding of the TMC-taurine chloride in dichloromethane to an aqueous solution of the corresponding amine (compound XXVI in reaction scheme II). After the addition, the reaction mixture is stirred for 2–5 hr, preferably for 2 hr at room temperature (20–25° C.), the organic solvent is evaporated, water is added and the products are extracted with a suitable organic medium such as chloroform. The organic fraction is dried using a drying agent such as Na2SO4 or MgSO4, filtered, evaporated and the products are crystallized using chloroform:hexane mixtures to get the desirable product. The chemical structures are identified by elemental analysis and spectroscopic methods.

Workup

  1. customThe water is evaporated
  2. extractionthe product is extracted
  3. filtrationThe insoluble salts are filtered off
  4. customTMC-taurine is crystallized
  5. additionAfter the addition
  6. stirringthe reaction mixture is stirred for 2–5 hr, preferably for 2 hr at room temperature (20–25° C.)
  7. customthe organic solvent is evaporated
  8. additionwater is added
  9. extractionthe products are extracted with a suitable organic medium such as chloroform
  10. customThe organic fraction is dried
  11. filtrationfiltered
  12. customevaporated
  13. customthe products are crystallized
  14. customhexane mixtures to get the desirable product

Sources & evidence

ORD record
ord-b896b06d14dc4e5a878315baca9d04bf
Source dataset
uspto-grants-2007_06
Patent number
US07232929B2

Reaction notes

Loading…