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

HRID 469449

Reaction equation

HRID 469449 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 585569892-(2-Carbamoylthiophen-3-ylamino)-2-phenylacetic acidYield 70.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e9f8c34ea1a948a480eff70d7cb1f441
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Linked notes

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