Beta-Alanine → Epimerox

HRID 409357Notes

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:21]=[C:22]([C:27]2S[C:30]([CH:32]=O)=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]=1[Cl:26].NCCC(O)=[O:38].CO.C(Cl)Cl>C(O)(=O)C>[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[O:38][C:30](/[CH:32]=[C:3]3/[NH:4][C:5](=[S:18])[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:2]/3=[O:1])=[CH:29][CH:28]=2)[CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)-3-phenylpropanoic acid (0.110g, 0.416 mmol) and 5-(3,4-dichloro-phenyl)thiophene-2-carbaldehyde (0.100 g, 0.416 mmol) in acetic acid 10 mL is added β-alanine (1.8 mg, 0.021 mmol) and heat to 80° C. for 16 h. The resulting reaction mixture is cooled down and the solvent is removed. The pure product (0.070 g, 0.144 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. The product is further purified by recryatallization in hexane and DCM mixture and got pure E-isomer. 1H-NMR (CDCl3/CD3OD/300 MHz): 7.84 (d, J=2.1 Hz, 1H), 7.60 (dd, J=8.7, 2.4 Hz, 1H), 7.44 (d, J=2.7 Hz, 1H), 7.17 (m, 6H), 6.85 (m, 1H), 6.42 (s, 1H), 5.61 (dd, J=11.1, 5.4 Hz, 1H), 3.66 (dd, J=14.1, 12.6 Hz, 1H), 3.53 (dd, J=14.1, 5.1 Hz, 1H). MS (ES−, m/z): 585.3 (M−, 100.0).

Workup

customThe resulting reaction mixture
temperatureis cooled down
customthe solvent is removed
customThe pure product (0.070 g, 0.144 mmol, red solid) is obtained by column chromatography
customThe product is further purified by recryatallization in hexane

Sources & evidence

ORD record: ord-6aa79c135c52472b85f5ea4333c37c3d
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759384B2

Reaction notes

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