Beta-Alanine → 3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoic acid

HRID 2214517Notes

Reaction equation

COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[NH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27].[Cl:29][C:30]1[CH:31]=[C:32]([CH:46]=[CH:47][C:48]=1[Cl:49])[CH2:33][N:34]([CH3:45])[C:35]([C:37]1[CH2:38]N(C)[C:40](=[O:43])[C:41]=1[OH:42])=[O:36]>>[Cl:29][C:30]1[CH:31]=[C:32]([CH:46]=[CH:47][C:48]=1[Cl:49])[CH2:33][N:34]([CH3:45])[C:35]([C:37]1[CH2:38][N:23]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[C:40](=[O:43])[C:41]=1[OH:42])=[O:36]

Participants

Reactant 4

HCID 239Beta-Alanine

HCID 712Formaldehyde

HCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamide

HCID 69655739HCID 69655739, compound2×

Product 1

HCID 546917463-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoic acidYield 25%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and β-alanine as described in the preparation of Compound 12. The resulting residue was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as an amber solid (48.5 mg, 25% yield). Mp=183–184° C. 1H NMR (500 MHz, DMSO) δ: 12.34 (s, 2H), 10.79 (s, 1H), 7.61 (d, 1H, J=8.54), 7.51 (s, 1H), 7.24 (bs, 1H), 4.57 (s, 2H), 4.06 (s, 2H), 3.58 (t, 2H, J=6.40), 2.96 (bs, 3H), 2.54 (t, 2H, J=7.02). HRMS (M−H) calcd for C16H15N2Cl2O5: 385.0358. found: 385.0364.

Workup

customThe resulting residue was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record: ord-5a3d4d8fea1041668b5c4a55a7659cc3
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109186B2

Reaction notes

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