Diethyl acetylenedicarboxylate → HCID 178472253, compound

HRID 1093047Notes

Reaction equation

HRID 1093047 reaction equation
C([O:4][CH2:5][C@@H:6]1[C@@H:11](OC(=O)C)[CH:10]=[CH:9][C@H:8]([C:16](=[NH:19])[NH:17][OH:18])[O:7]1)(=O)C.[CH2:20]([O:22][C:23]([C:25]#[C:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])[CH3:21]>CCO>[OH:4][CH2:5][C@H:6]1[O:7][C@@H:8]([C:16](=[NH:19])[NH:17][O:18]/[C:26](=[CH:25]/[C:23]([O:22][CH2:20][CH3:21])=[O:24])/[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 178476348HCID 178476348, compound

Product 1

HCID 178472253HCID 178472253, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To ((2R,3S,6R)-3-acetoxy-6-(N-hydroxycarbamimidoyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (2.33 g, 13.4 mmol) in EtOH (15 mL) was added diethylacetylenedicarboxylate (3.20 mL, 20.1 mmol) and the reaction mixture was stirred at 60° C. for 3 h. The solvent was removed in vacuo to afford 2.40 g (52% yield) of the title compound as an amber oil. LCMS (+ESI, M+H+) m/z 345.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1fd960ecb06a441b8c4796173584d261
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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