Sodium Hydroxide → HCID 58557018, compound

HRID 469447Notes

Reaction equation

HRID 469447 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](=[O:22])[CH3:21].[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:22])[CH3:21]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 97780Ethyl bromophenylacetateHCID 27352332-Acetyl-3-aminothiophene

Product 1

HCID 58557018HCID 58557018, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 2-bromo-2-phenylacetate (349 μl, 2.00 mmol) and 1-(3-aminothiophen-2-yl)ethanone (282 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), and sodium hydroxide (80.0 mg, 2.00 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, and then ethanol was evaporated under vacuum. The residue was taken up with water and washed with EtOAc. The pH of the aqueous phase was adjusted to 3 with HCl, and the aqueous phase was back-extracted with EtOAc. The organic phase was dried over Na2SO4, filtered and evaporated to dryness to obtain 2-(2-acetylthiophen-3-ylamino)-2-phenylacetic acid (188 mg, 34% 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. customethanol was evaporated under vacuum
  4. washwashed with EtOAc
  5. extractionthe aqueous phase was back-extracted with EtOAc
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-c72d84c2171b4c7c86332128a3b6233d
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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