Tetrahydrofuran → HCID 86591894, compound

HRID 1883113Notes

Reaction equation

HRID 1883113 reaction equation
[O-]CC.[Na+].[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:19])[O:15][CH2:16][CH:17]=[CH2:18])=[CH:9][CH:8]=1)=O.[CH2:20]([O:22][C:23](=[O:28])[CH2:24][N:25]=[N+:26]=[N-:27])[CH3:21].O1CCCC1>C(O)C>[CH2:16]([O:15][C:14]([NH:13][C:10]1[CH:11]=[CH:12][C:7](/[CH:5]=[C:24](/[N:25]=[N+:26]=[N-:27])\[C:23]([O:22][CH2:20][CH3:21])=[O:28])=[CH:8][CH:9]=1)=[O:19])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 69480Acetic acid, azido-, ethyl esterHCID 2723922Sodium ethoxideHCID 11481140HCID 11481140, compound

Product 1

HCID 86591894HCID 86591894, compoundYield 49.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 689 mg (10.13 mmol) sodium ethoxide in 5 mL absolute ethanol at 0° C. was added a solution of 500 mg (2.44 mmol) of allyl 4-formylphenylcarbamate and 1.25 g (9.75 mmol) ethylazidoacetate dissolved in 5 mL absolute ethanol and 1 mL tetrahydrofuran dropwise over 5 minutes. The mixture was stirred at 0° C. for 1.5 h, then partitioned between ethyl acetate and 1 N HCl until neutral. The organic phase was dried over magnesium sulfate, concentrated and purified by column chromatography, eluting with 25% ethyl acetate/hexane to provide 385 mg of ethyl (2E)-3-(4-{[(allyloxy)carbonyl]amino}phenyl)-2-azidoprop-2-enoate as a yellow solid.

Workup

  1. custompartitioned between ethyl acetate and 1 N HCl until neutral
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. custompurified by column chromatography
  5. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed226d474a8049059fa5bda1657f4b06
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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