Dimethylformamide → HCID 10498045, compound

HRID 361754Notes

Reaction equation

HRID 361754 reaction equation
Cl.[CH2:2]([CH:10]([C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])[NH2:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([N:20]([CH2:23][CH3:24])CC)C.CN([CH:28]=[O:29])C>>[C:23]([C:24]1[CH:12]=[CH:10][C:2]([C:28]([NH:11][CH:10]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:12]([CH3:17])([CH3:16])[C:13]([OH:15])=[O:14])=[O:29])=[CH:3][CH:4]=1)#[N:20]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 70203039HCID 70203039, compound

Product 1

HCID 10498045HCID 10498045, compound

Procedure

β-Phenethyl-α,α-dimethyl-β-alanine hydrochloride (600 mg, 2.33 mmol) was dissolved in DMF (100 ml). To the resulting solution, triethylamine (Et3N) (0.98 ml, 6.99 mmol) and 4-cyanobenzoyl-OSu (630 mg, 2.56 mmol) were added under cooling with ice and the mixture was stirred at room temperature overnight. After the solvent was distilled off, the residue was dissolved in a 2N aqueous solution of sodium carbonate and washed with hexane. The aqueous layer was adjusted to pH 3 with citric acid and extracted with ethyl acetate. The collected ethyl acetate layer was washed with a saturated aqueous solution of NaCl and dried over anhydrous sodium sulfate. After the solvent was distilled off, the obtained crude N-4-cyanobenzoyl-β-phenethyl-α,α-dimethyl-β-alanine (200 mg, 0.57 mmol) was derivatized to N-4-cyanobenzoyl-β-phenethyl-α,α-dimethyl-β-alanyl-4-piperidineacetic acid benzyl ester (212 mg, 65.8%) by the same procedure as in Example 2-(6-2).

Workup

  1. temperatureunder cooling with ice
  2. distillationAfter the solvent was distilled off
  3. dissolutionthe residue was dissolved in a 2N aqueous solution of sodium carbonate
  4. washwashed with hexane
  5. extractionextracted with ethyl acetate
  6. washThe collected ethyl acetate layer was washed with a saturated aqueous solution of NaCl
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-357ad619cf914a2f845399e077a232a7
Source dataset
uspto-grants-1999_02
Patent number
US05866592

Reaction notes

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