Diethylamine → HCID 53705050, compound

HRID 1845762Notes

Reaction equation

HRID 1845762 reaction equation
[CH3:1][O:2][CH2:3][C:4](=[O:10])[CH2:5][C:6]([O:8][CH3:9])=[O:7].C1(C)C=CC(S([N:20]=[N+:21]=[N-])(=O)=O)=CC=1.C(NCC)C>CCOCC>[N+:20](=[C:5]([C:4](=[O:10])[CH2:3][O:2][CH3:1])[C:6]([O:8][CH3:9])=[O:7])=[N-:21]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 13661p-Toluenesulfonyl azideHCID 123500Methyl 4-methoxyacetoacetate

Product 1

HCID 53705050HCID 53705050, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 4-methoxy-3-oxobutanoate (4.28 g, 0.029 mol) was dissolved in ether (20 mL). The solution was cooled in an ice bath. To the solution was added p-toluenesulfonyl azide (5.78 g, 0.029 mol) followed by N-ethylethanamine (2.0 mL, 0.019 mol). The solution was stirred at 0° C. for 15 minutes, then at rt for 30 minutes. Upon evaporation, the tosyl amide bi-product solidified. This was filtered off and the filtrate was purified by flash chromatography to give the desired product (4.5 g, 89%) as a light oil. 1H NMR (400 MHz, CDCl3): δ 4.55 (s, 2H), 3.83 (s, 3H), 3.45 (s, 3H). MF C6H8N2O4. LCMS calculated for C6H9N2O4(M+H)+: m/z=173.0.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. waitat rt for 30 minutes
  3. customUpon evaporation
  4. filtrationThis was filtered off
  5. customthe filtrate was purified by flash chromatography

Sources & evidence

ORD record
ord-15e194b388fb44c4af7fdd9b97194df7
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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