Beta-Alanine → HCID 75039752, compound

HRID 409354Notes

Reaction equation

HRID 409354 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[C:5](=[S:18])[NH:4][CH2:3]1.[O:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH3:20].NCCC(O)=O.CO.C(Cl)Cl>C(O)(=O)C>[CH3:20][O:19][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[S:31][C:30]([CH:32]=[C:3]3[C:2](=[O:1])[N:6]([CH:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:8]([OH:10])=[O:9])[C:5](=[S:18])[NH:4]3)=[CH:29][CH:28]=2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 27978005-(4-methoxyphenyl)thiophene-2-carbaldehydeHCID 21226129Dichloromethane methanolHCID 57994057HCID 57994057, compound

Product 1

HCID 75039752HCID 75039752, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.080 g, 0.303 mmol) and 5-(4-methoxylphenyl)thiophene-2-carbaldehyde (0.066 g, 0.303 mmol) in acetic acid 5 mL is added β-alanine (2.69 mg, 0.030 mmol) and heat to 170° C. for 30 min under microwave irradiation. The resulting reaction mixture is cooled down and the solvent is removed. The pure product (0.075 g, 0.162 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.62 (m, 2H), 7.45 (m, 1H), 7.33 (m, 5H), 7.27 (d, J=13.2 Hz, 1H), 6.94 (d, J=6.9 Hz, 2H), 6.70 (s, 1H), 5.50 (m, 1H), 3.82 (s, 3H), 3.53 (m, 2H). MS (ES+, m/z): 465.1 (M++1, 20.0).

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled down
  3. customthe solvent is removed
  4. customThe pure product (0.075 g, 0.162 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-5bbc071632f74473b2a399a31e1d036c
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

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