Acetamidomalonic acid diethyl ester → HCID 14561225, compound

HRID 1698879Notes

Reaction equation

HRID 1698879 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][CH2:12]Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:14]([NH:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:16])[CH3:15].[O-]CC.[Na+].[Na]>C(O)C>[CH2:27]([O:26][C:24](=[O:25])[C:18]([NH:17][C:14](=[O:16])[CH3:15])([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:12][C:11]#[C:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:28]

Participants

6

Reactant 4

HCID 14041Acetamidomalonic acid diethyl esterHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14561224tert-Butyl (4-chlorobut-2-yn-1-yl)carbamate

Product 1

HCID 14561225HCID 14561225, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ex-8d) 12.1 g 1-t-Butyloxycarbonylamino-4-chloro-2-butyne is refluxed for 16 h with a mixture of 8 g diethyl acetamidomalonate and sodiumethoxide prepared from 900 mg of sodium in 100 mL of absolute ethanol. Ethanol is then removed under vacuum and the residual mass is partitioned between water and ethylacetate/ether (1:1). The organic layer is treated with 0.5N NaOH and 0.5N HCl and washed with water. It is then dried over Na2SO4, filtered and concentrated. The product is crystallized from ethylacetate/petroleum ether to give ˜7 g of Ethyl-2-acetylamino-6-t-butyloxycarbonylamino-2-ethoxycarbonyl-4-hexynoate.

Workup

  1. customEthanol is then removed under vacuum
  2. customthe residual mass is partitioned between water and ethylacetate/ether (1:1)
  3. additionThe organic layer is treated with 0.5N NaOH and 0.5N HCl
  4. washwashed with water
  5. dry with materialIt is then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product is crystallized from ethylacetate/petroleum ether

Sources & evidence

ORD record
ord-cb0e4b75da964350aa8ee2be15f10f1a
Source dataset
uspto-grants-2002_02
Patent number
US06344483B1

Reaction notes

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