Sodium Hydroxide → 2-(2-Carbamoylthiophen-3-ylamino)-2-phenylacetic acid

HRID 469449

Reaktionsgleichung

Reaktionsgleichung von HRID 469449
Br[CH:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]CC)=[O:4].[NH2:14][C:15]1[CH:19]=[CH:18][S:17][C:16]=1[C:20]([NH2:22])=[O:21].[OH-].[Na+]>C(#N)C>[C:20]([C:16]1[S:17][CH:18]=[CH:19][C:15]=1[NH:14][CH:2]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:3]([OH:5])=[O:4])(=[O:21])[NH2:22]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 97780Ethyl bromophenylacetateHCID 5189933-Aminothiophene-2-carboxamide

Produkt 1

HCID 585569892-(2-Carbamoylthiophen-3-ylamino)-2-phenylacetic acidAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-bromo-2-phenylacetate (349 μl, 2.00 mmol) and 3-aminothiophene-2-carboxamide (284 mg, 2.00 mmol) in acetonitrile (2 ml) was heated under microwave irradiation at 100° C. for 1 hour. Acetonitrile was evaporated, and the residue was dissolved in EtOH (2 ml). Sodium hydroxide (80 mg, 2.00 mmol) was added, and the reaction mixture was stirred at room temperature for 24 hours. Then ethanol was evaporated, and the residue was taken up with water and washed with EtOAc. The pH of the aqueous phase was adjusted to 3 with HCl, and product was extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to obtain 2-(2-carbamoylthiophen-3-ylamino)-2-phenylacetic acid (389 mg, 70% yield), which was used in the next step without any further purification.

Aufarbeitung

  1. customAcetonitrile was evaporated
  2. dissolutionthe residue was dissolved in EtOH (2 ml)
  3. customThen ethanol was evaporated
  4. washwashed with EtOAc
  5. extractionwas extracted with EtOAc
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-e9f8c34ea1a948a480eff70d7cb1f441
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629160B2

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