Hydrochloric Acid → HCID 178500136, compound

HRID 486486Notes

Reaction equation

HRID 486486 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7])#[N:2].C([Sn]([N:29]=[N+:30]=[N-:31])(CCCC)CCCC)CCC.Cl>CO>[C:10]1([CH:5]([CH2:4][CH2:3][C:1]2[NH:31][N:30]=[N:29][N:2]=2)[C:6]([O:8][CH3:9])=[O:7])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 53645094Methyl (RS)-4-cyano-2-phenylbutanoate

Product 1

HCID 178500136HCID 178500136, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

Methyl (RS)-4-cyano-2-phenylbutanoate (see Preparation 21) (1.8 g) and tri-n-butyltin azide (3.23 g were mixed and heated at 160° C. for 3 hours, dissolved in methanol (100 ml), treated by the addition of hydrogen chloride gas for 10 minutes and left for 18 hours. Evaporation gave a residue which was triturated three times with diisopropyl ether then partitioned between 10% aqueous sodium carbonate and ethyl acetate. The aqueous later was acidifed with 2 M hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulphate and evaporated to give the title compound (1.34 g, 61%) as a brown oil.

Workup

  1. customEvaporation
  2. customgave a residue which
  3. customwas triturated three times with diisopropyl ether
  4. customthen partitioned between 10% aqueous sodium carbonate and ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-6451df9b56e34fc1b070a1adfb951852
Source dataset
uspto-grants-1994_03
Patent number
US05292749

Reaction notes

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