Beta-Alanine → HCID 75038379, compound

HRID 409366Notes

Reaction equation

HRID 409366 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])[C:5](=[S:13])[NH:4][CH2:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2S[C:25]([CH:27]=O)=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[Cl:21].NCCC(O)=[O:33].CO.C(Cl)Cl>C(O)(=O)C>[Cl:14][C:15]1[CH:16]=[C:17]([C:22]2[O:33][C:25]([CH:27]=[C:3]3[C:2](=[O:1])[N:6]([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])[C:5](=[S:13])[NH:4]3)=[CH:24][CH:23]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 16768839HCID 16768839, compoundHCID 21226129Dichloromethane methanolHCID 86636692HCID 86636692, compound

Product 1

HCID 75038379HCID 75038379, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 2-(5-oxo-2-thioxoimidazolidin-1-yl)butanoic acid (0.130 g, 0.643 mmol) and 5-(3,4-dichloro-phenyl)thiophene-2-carbaldehyde (0.155 g, 0.643 mmol) in acetic acid 5 mL is added β-alanine (5.72 mg, 0.064 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, 0.141 mmol, red solid) is obtained by column chromatography using MeOH/DCM, 2-7% ration solvent system. 1H-NMR (CD3OD/300 MHz): 7.97 (d, J=2.1 Hz, 1H), 7.68 (dd, J=8.4, 2.1 Hz, 1H), 7.49 (d, J=4.8 Hz, 1H), 7.02 (m, 2H), 6.48 (s, 1H), 5.31 (dd, J=11.1, 5.4 Hz, 1H), 2.32 (m, 2H), 0.93 (t, J=7.2 Hz, 3H). MS (ES−, m/z): 423.3 (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, 0.141 mmol, red solid) is obtained by column chromatography

Sources & evidence

ORD record
ord-d0d19d2984f94d4d85abbfb70add570a
Source dataset
uspto-grants-2014_06
Patent number
US08759384B2

Reaction notes

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