Triethylamine → HCID 20349895, compound

HRID 1430715Notes

Reaction equation

HRID 1430715 reaction equation
[C:1](/[C:3](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)/[C:4]([O:6][CH2:7][CH:8]1[CH2:12][O:11]C(C)(C)[O:9]1)=[O:5])#[N:2].C(N(CC)CC)C>C1COCC1.CO>[C:1](/[C:3](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1)/[C:4]([O:6][CH2:7][CH:8]([OH:9])[CH2:12][OH:11])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 68331125HCID 68331125, compound

Product 1

HCID 20349895HCID 20349895, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Compound 13 (0.5 g, 1.5 mmol) was dissolved in a mixture of THF/MeOH (1:1) and DOWEX-H+ resin (0.10 g) was added and the heterogeneous mixture was stirred for 20 hours. The DOWEX-H+ resin was removed by filtration and triethylamine (50 mg, 0.5 mmol) was added and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (100% ether) to give compound 14. 14: 75% yield; bright yellow solid; 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.94 (d, 2H, J=9.1 Hz), 6.69 (d, 2H, J=9.2 Hz), 4.42-4.32 (m, 2H), 4.05 (m, 1H), 3.80-3.70 (m, 2H), 3.12 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 199.0, 164.8, 155.5, 154.0, 134.6, 119.4, 117.9, 111.8, 111.7, 92.8, 70.3, 70.2, 66.9, 66.8, 63.6, 63.5, 40.3, 40.2; HRMS Calc for C15H18N2O4 (M+H)+ 291.1345 Found 291.1361.

Workup

  1. additionwas added
  2. additionwas added
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by flash chromatography (100% ether)

Sources & evidence

ORD record
ord-50568c482b86457f959547f56c53c1fb
Source dataset
uspto-grants-2015_01
Patent number
US08940918B2

Reaction notes

Loading…