Acetic Acid → HCID 66652938, compound

HRID 572565Notes

Reaction equation

HRID 572565 reaction equation
C([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)(=O)C.[NH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[CH3:21][C:22](O)=O.[BH4-].[Na+]>C1(C)C=CC=CC=1>[C:8]([C:7]1[CH:10]=[C:11]([CH:21]([NH:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH3:22])[CH:4]=[CH:5][CH:6]=1)#[N:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 740444'-CyanoacetophenoneHCID 151417Glycine tert-butyl esterHCID 4311764Sodium borohydride

Product 1

HCID 66652938HCID 66652938, compoundYield 80.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

4-Acetylbenzonitrile (1.0 g; 6.9 mmol) and tert-butyl glycinate (1.2 g; 9.0 mmol) were dissolved in toluene (20 mL). The mixture was stirred at reflux with a Dean-Stark trap. AcOH (207 μL; 3.4 mmol) was added and the mixture was further heated overnight. Solvents were evaporated. The crude was dissolved in MeOH (35 mL). The solution was cooled down to 0° C. and sodium borohydride (781 mg; 21 mmol) was added in portions. The reaction was stirred at 0° C. for 1 h and was let stirred at RT overnight. Solvents were evaporated. The crude residue was suspended in EtOAc, washed with NH4Cl saturated solution, NaHCO3 saturated solution, brine and dried over MgSO4. After evaporation of the solvents the resulting yellow oil was purified by flash chromatography affording the title compound 716 mg as a colorless oil. LC/MS (Method B): 261.0 (M+H)+. HPLC (Method A) Rt 2.79 min (Purity: 99.2%).

Workup

  1. temperatureat reflux with a Dean-Stark trap
  2. temperaturethe mixture was further heated overnight
  3. customSolvents were evaporated
  4. dissolutionThe crude was dissolved in MeOH (35 mL)
  5. stirringThe reaction was stirred at 0° C. for 1 h
  6. stirringwas let stirred at RT overnight
  7. customSolvents were evaporated
  8. washwashed with NH4Cl saturated solution, NaHCO3 saturated solution, brine
  9. dry with materialdried over MgSO4
  10. customAfter evaporation of the solvents the resulting yellow oil
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-53bdaba0985c4f8c9c5d0d4a9b4060fd
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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