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

HRID 2067651Notes

Reaction equation

HRID 2067651 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-0ddc47e3b6bd43e5af31d953233cc850
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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