Diethyl acetylenedicarboxylate → HCID 86634931, compound

HRID 1093062Notes

Reaction equation

HRID 1093062 reaction equation
[NH2:1][C:2](=[N:23][OH:24])[CH:3]([N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:4]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5]1.[CH2:25]([O:27][C:28]([C:30]#[C:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:29])[CH3:26]>CCO>[NH2:1][C:2](=[N:23][O:24]/[C:31](=[CH:30]/[C:28]([O:27][CH2:25][CH3:26])=[O:29])/[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:3]([N:11]([C:12]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:21])[CH3:22])[CH:4]1[CH2:8][CH2:7][CH:6]([CH2:9][OH:10])[CH2:5]1

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 76637589HCID 76637589, compound

Product 1

HCID 86634931HCID 86634931, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

To benzyl 2-amino-2-(hydroxyimino)-1-(3-(hydroxymethyl)cyclopentyl)ethyl(methyl)carbamate (0.800 g, 1.78 mmol) in EtOH (40 mL) was added diethylacetylenedicarboxylate (0.428 ml, 2.67 mmol). The reaction mixture was stirred at 23° C. for 2 days. The solvent was removed in vacuo and the crude material purified on a Silica gel column (Biotage flash chromatography system), eluted with a gradient of ethyl acetate:hexane (1:5) to (1:1) to afford 0.570 g (52% yield) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.33-7.42 (5 H, m), 5.17-5.25 (3 H, m), 4.12-4.40 (4 H, m), 3.55 (2 H, m), 2.83-2.94 (4 H, m), 2.70-2.75 (1 H, m), 2.17-2.09 (2 H, m), 1.82-2.00 (3 H, m), 1.21-1.342 (7 H, m). LCMS (+ESI, M+H+) m/z 506.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material purified on a Silica gel column (Biotage flash chromatography system)
  3. washeluted with a gradient of ethyl acetate:hexane (1:5) to (1:1)

Sources & evidence

ORD record
ord-13bb38c9b3f241f1abad06e78a8cf128
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

Loading…