Beta-Alanine → HCID 75039751, compound

HRID 409353Notes

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.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:30][C:29]([CH:31]=O)=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.NCCC(O)=O.CO.C(Cl)Cl>C(O)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[S:30][C:29]([CH:31]=[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:28][CH:27]=2)=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.080 g, 0.304 mmol) and 5-(4-chorophenyl)thiophene-2-carbaldehyde (0.068 g, 0.304 mmol) in acetic acid 5 mL is added β-alanine (2.7 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 (0.110 g, 0.235 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.66 (dd, J=8.7, 1.5 Hz, 2H), 7.50 (dm, J=12.6 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 7.18 (m, 5H), 6.69 (s, 1H), 5.65 (dd, J=12.0, 4.5 Hz, 1H), 3.68 (dd, J=13.8, 12.0 Hz, 1H), 3.51 (dd, J=14.4, 4.5 Hz, 1H). MS (ES+, m/z): 469.5 (M++1, 30.0).

Workup

customThe resulting reaction mixture
temperatureis cooled down
customthe solvent is removed
customThe pure product (0.110 g, 0.235 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record: ord-e0f5ad537ea94a7f9316fb9c38f5d4a8
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759384B2

Reaction notes

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