Beta-Alanine → HCID 76698629, compound

HRID 409356Notes

Reaction equation

HRID 409356 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[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:23]=[CH:24][C:25]=1[Cl:26]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 16768839HCID 16768839, compoundHCID 21226129Dichloromethane methanolHCID 57994057HCID 57994057, compound

Product 1

HCID 76698629HCID 76698629, 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 (0.055 g, 0.207 mmol) and 5-(3,4-dichloro-phenyl)thiophene-2-carbaldehyde (0.050 g, 0.207 mmol) in acetic acid 5 mL is added β-alanine (1.8 mg, 0.021 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 (0.060 g, 0.123 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 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 (m, 1H), 3.53 (m, 1H). MS (ES−, m/z): 585.3 (M−, 100.0).

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled down
  3. customthe solvent is removed
  4. customThe pure product (0.060 g, 0.123 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-6e752bc0d5214a93b845ce0181428ac5
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

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