Acetic Acid → HCID 54936468, compound

HRID 572562Notes

Reaction equation

HRID 572562 reaction equation
C(C1C=CC(C#N)=CC=1)(=O)C.NCC(OC(C)(C)C)=O.CC(O)=O.[C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33](=[N:35][CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:34])=[CH:29][CH:28]=1)#[N:26].[BH4-].[Na+]>C1(C)C=CC=CC=1.CO>[C:25]([C:27]1[CH:28]=[CH:29][C:30]([CH:33]([NH:35][CH2:36][C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH3:34])=[CH:31][CH:32]=1)#[N:26]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 740444'-CyanoacetophenoneHCID 151417Glycine tert-butyl esterHCID 4311764Sodium borohydrideHCID 86683833HCID 86683833, compound

Product 1

HCID 54936468HCID 54936468, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

4-acetylbenzonitrile (500 mg; 3.4 mmol; 1 eq.) and tert-butyl glycinate (588 mg; 4.5 mmol) were dissolved in toluene (10 mL). AcOH (103 μl; 1.7 mmol) was added. The mixture was stirred at reflux with a dean stark trap overnight. Solvents were evaporated and the resulting tert-butyl N-[1-(4-cyanophenyl)ethylidene]glycinate (889 mg; 3.4 mmol) was dissolved in MeOH (18 mL). Sodium borohydride (390 mg; 10.3 mmol) was added in portions, resulting in an exothermic reaction (reflux). The reaction was 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 as a colorless oil. LC/MS (Method B): 261.0 (M+H)+. HPLC (Method A): 2.77 min (purity: 98.2%).

Workup

  1. temperatureat reflux with a dean stark trap overnight
  2. customSolvents were evaporated
  3. customresulting in an exothermic reaction (reflux)
  4. stirringThe reaction was stirred at RT overnight
  5. customSolvents were evaporated
  6. washwashed with NH4Cl saturated solution, NaHCO3 saturated solution, brine
  7. dry with materialdried over MgSO4
  8. customAfter evaporation of the solvents the resulting yellow oil
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-602ab434ea134ed4917071f31ee56d2c
Source dataset
uspto-grants-2015_05
Patent number
US09029405B2

Reaction notes

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