Hydrochloric Acid → HCID 178471279, compound

HRID 620234Notes

Reaction equation

HRID 620234 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:2].C([Sn]([N:24]=[N+:25]=[N-:26])(CCCC)CCCC)CCC.Cl>COCCOC.CO>[NH:24]1[C:1]([CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:2][N:26]=[N:25]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4984872Tributyltin azideHCID 10997123Ethyl 4-cyanobutanoate

Product 1

HCID 178471279HCID 178471279, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Ethyl 4-cyanobutyrate (approximately 15 g) was dissolved in DME. Tris(n-butyl)tin azide (5 ml) was added and the reaction solution was heated to 85° overnight then cooled to room temperature. The cooled solution was diluted with methanol (20 ml) then 1N hydrochloric acid (20 ml) was added. The solution was stirred for one hour then partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed by preparatory-scale HPLC (silcia column) eluted with a gradient of 30 to 70% ethyl acetate in hexane plus 1% acetic and to yield 3.39 g of the title product: n.m.r.(300 MHz, CDCl3) δ: 4.2 (q, 2H); 2.95 (t, 2H); 2.5 (t, 2H); 2.1 (t, 2H); 1.3 (t, 3H).

Workup

  1. temperaturethe reaction solution was heated to 85° overnight
  2. customthen partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed by preparatory-scale HPLC (silcia column)
  7. washeluted with a gradient of 30 to 70% ethyl acetate in hexane plus 1% acetic

Sources & evidence

ORD record
ord-47bdb3b3f67843578b30814cd6ca1af9
Source dataset
uspto-grants-1989_04
Patent number
US04820723

Reaction notes

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