Triethylamine → HCID 56622760, compound

HRID 1905093Notes

Reaction equation

HRID 1905093 reaction equation
C(N(CC)CC)C.[CH2:8]([O:15][CH2:16][C:17](=[O:26])[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC(S([N:36]=[N+:37]=[N-])(=O)=O)=CC=1>C(#N)C>[CH2:8]([O:15][CH2:16][C:17](=[O:26])[C:18](=[N+:36]=[N-:37])[C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 12035485Butanoic acid, 3-oxo-4-(phenylmethoxy)-, 1,1-dimethylethyl ester

Product 1

HCID 56622760HCID 56622760, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

5.54 ml (40 mmol - 2 equivalents) of triethylamine were added dropwise to a solution, which had been cooled to 0° C., of 5.29 g (20 mmol) of tert.-butyl 4-benzyloxyacetoacetate and 4.34 g (22 mmol) of p-toluenesulphonyl azide in 40 ml of anhydrous acetonitrile. The mixture was stirred at 0° C. for 30 min, 8 g of kieselguhr were added, and evaporation in vacuo and chromatography on 100 g of silica gel (toluene:ethyl acetate 95:5) were carried out. 3.98 g (69%) of the title compound were obtained as colorless crystals, melting point: 68° C., Rf: 0.31 (toluene:ethyl acetate 95:5).

Workup

  1. addition8 g of kieselguhr were added
  2. customevaporation in vacuo and chromatography on 100 g of silica gel (toluene:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-6c051703d2774d8492ed4de398a5acc3
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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