Triethylamine → HCID 12798029, compound

HRID 1106025Notes

Reaction equation

HRID 1106025 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11](Cl)=[O:12])=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[CH:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]2[CH:29]=[C:28]([CH:30]([OH:33])[C:31]#[N:32])[CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH:14]([CH3:16])[CH3:15])[C:11]([O:33][CH:30]([C:31]#[N:32])[C:28]2[CH:27]=[CH:26][CH:25]=[C:24]([O:23][C:20]3[CH:19]=[CH:18][CH:17]=[CH:22][CH:21]=3)[CH:29]=2)=[O:12])=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-HCID 12798028HCID 12798028, compound

Product 1

HCID 12798029HCID 12798029, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(4-Azidophenyl)-3-methylbutanoyl chloride, prepared in Example 7, was dissolved in 10 ml of methylene chloride. A solution of 3.79 g of m-phenoxybenzaldehyde cyanohydrin in 10 ml of methylene chloride was added, with cooling by an ice bath, followed by 2.4 ml of triethylamine, causing an exothermic reaction and precipitating white solid. After an hour without cooling, the mixture was evaporated to a residue, which was extracted with diethyl ether, the extract filtered, and the filtrate washed with water and saturated sodium bicarbonate solution, dried (MgSO4), and evaporated to 7.4 g of residual oil, 2-(4-azidophenyl)-3-methylbutanoic acid, α-cyano-3-phenoxybenzyl ester. The infrared spectrum shows absorption peaks at 2130 cm-1 (azide) and 1760 cm-1 (ester carbonyl). Mass spectral analysis showed a molecular ion, m/e 426, corresponding to the product.

Workup

  1. temperaturewith cooling by an ice bath
  2. customan exothermic reaction
  3. customprecipitating white solid
  4. temperatureAfter an hour without cooling
  5. customthe mixture was evaporated to a residue, which
  6. extractionwas extracted with diethyl ether
  7. filtrationthe extract filtered
  8. washthe filtrate washed with water and saturated sodium bicarbonate solution
  9. dry with materialdried (MgSO4)
  10. customevaporated to 7.4 g of residual oil, 2-(4-azidophenyl)-3-methylbutanoic acid, α-cyano-3-phenoxybenzyl ester
  11. customabsorption peaks at 2130 cm-1 (azide) and 1760 cm-1 (ester carbonyl)

Sources & evidence

ORD record
ord-c4d72b068a4948e78b6138f1459ecc8e
Source dataset
uspto-grants-1982_01
Patent number
US04311696

Reaction notes

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