Hydrochloric Acid → 2-(2-Oxopyrrolidin-1-yl)-2-phenylacetic acid

HRID 404665Notes

Reaction equation

HRID 404665 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([OH:11])=[O:10])=[O:6].CC(C)([O-])C.[K+].Cl>C1COCC1.O>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 866889262-(4-Chlorobutanamido)-2-phenylacetic acid

Product 1

HCID 132542962-(2-Oxopyrrolidin-1-yl)-2-phenylacetic acidYield 63.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-Chlorobutanamido)-2-phenylacetic acid (650 mg, 2.54 mmol) was dissolved in dry THF (8.5 ml) and the solution was cooled to 0° C. with an ice-bath stirring under nitrogen atmosphere. Potassium tert-butoxide (599 mg, 5.34 mmol) was added in three portions and a white suspension was obtained. The mixture was stirred at the same temperature for 15 minutes. 1N HCl was added dropwise till pH 2-3 and than the mixture was diluted with water (10 ml) and extracted three times with EtOAc (15 ml×3). The organic phase was dried (Na2SO4) and evaporated to obtain the title compound (352 mg, 63.2% yield) as a pale yellow spongy sticky solid.

Workup

  1. customa white suspension was obtained
  2. stirringThe mixture was stirred at the same temperature for 15 minutes
  3. extractionextracted three times with EtOAc (15 ml×3)
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-40fc3a5568e54e078c00a86c71480509
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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