2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile → HCID 19956408, compound

HRID 1779530Notes

Reaction equation

HRID 1779530 reaction equation
[C:1]([O:8]N=C(C1C=CC=CC=1)C#N)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.[NH2:19][CH2:20][CH2:21][CH2:22][NH:23][CH2:24]/[CH:25]=[CH:26]/[CH2:27][NH:28][CH2:29][CH2:30][CH2:31][NH2:32]>C1COCC1>[C:1]([NH:32][CH2:31][CH2:30][CH2:29][N:28]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:8])[CH2:27]/[CH:26]=[CH:25]/[CH2:24][N:23]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:8])[CH2:22][CH2:21][CH2:20][NH:19][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:8])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:8]

Participants

4

Reactant 2

HCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 5869833N,N'-BIS(3-AMINOPROPYL)-2-BUTENE-1,4-DIAMINE

Product 1

HCID 19956408HCID 19956408, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 25.86 g (105 mmol) of 2-(BOC-oxyimino)-2-phenylacetonitrile (Fluka, Switzerland) in 70 ml of THF is added dropwise over a period of 2 h, with stirring, to a solution, cooled to 5° C., of 5.01 g (25 mmol) of (E)-1,5,10,14-tetraazatetradec-7-ene in 50 ml of THF. The reaction mixture is stirred for a further 16 h at room temperature and is then concentrated by evaporation in vacuo. The residue is purified by flash chromatography, over silica gel having an average particle size of 0.04-0.063 mm, using ethyl acetate-hexane (1:3). Concentration of the product-containing fractions by evaporation yields the resinous title compound, Rf value=0.33 (silica gel/ethyl acetate:hexane (1:1)).

Workup

  1. stirringThe reaction mixture is stirred for a further 16 h at room temperature
  2. concentrationis then concentrated by evaporation in vacuo
  3. customThe residue is purified by flash chromatography, over silica gel having an average particle size of 0.04-0.063 mm
  4. customConcentration of the product-containing fractions by evaporation

Sources & evidence

ORD record
ord-54bec2c5b30a484c81b0359551ea9415
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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