HCID 58031619, compound → Ethyl 5-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

HRID 560872Notes

Reaction equation

HRID 560872 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][N:13]([C:16]2[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:26])[CH:17]=2)[C:12]1=[O:27])(C(C)(C)C)(C)C>C(O)(=O)C>[OH:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][N:13]([C:16]2[S:20][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:18]([CH3:26])[CH:17]=2)[C:12]1=[O:27]

Participants

3

Reactant 1

HCID 58031619HCID 58031619, compound

Product 1

HCID 58031585Ethyl 5-(3-(2-hydroxyethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl 5-(3-(2-(tert-butyldimethylsilyloxy)ethyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate (1.09 g 2.63 mmol) in acetic acid (10 mL) was stirred at 40° C. for 64 h. The reaction mixture was allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate and then with 5% methanol in dichloromethane to afford the title compound as a colorless solid in 78% yield (0.62 g): 1H NMR (300 MHz, CDCl3) δ 6.15 (s, 1H), 4.27 (q, J=7.1 Hz, 2H), 3.89-3.82 (m, 4H), 3.74-3.67 (m, 2H), 3.49-3.44 (m, 2H), 2.49 (s, 3H), 2.34 (t, J=5.3 Hz, 1H), 1.33 (t, J=7.1 Hz, 3H); MS (ES+) m/z 299.2 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column chromatography
  3. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-3b2efe32dc514bb9967a8155b93f1022
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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