Formaldehyde → 2-{4-[(3,4-Dichloro-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-succinamic acid

HRID 2214523Notes

Reaction equation

HRID 2214523 reaction equation
COC(=O)C(O)=CC(=O)N(CC1C=CC(Cl)=C(Cl)C=1)C.C=O.[NH2:23][C@H:24]([C:29]([OH:31])=[O:30])[CH2:25][C:26](=[O:28])[NH2:27].[Cl:32][C:33]1[CH:34]=[C:35]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:36][N:37]([CH3:48])[C:38]([C:40]1[CH2:41]N(C)[C:43](=[O:46])[C:44]=1[OH:45])=[O:39]>>[Cl:32][C:33]1[CH:34]=[C:35]([CH:49]=[CH:50][C:51]=1[Cl:52])[CH2:36][N:37]([CH3:48])[C:38]([C:40]1[CH2:41][N:23]([CH:24]([CH2:25][C:26]([NH2:27])=[O:28])[C:29]([OH:31])=[O:30])[C:43](=[O:46])[C:44]=1[OH:45])=[O:39]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 6267(-)-AsparagineHCID 54697551N-[(3,4-dichlorophenyl)methyl]-4-hydroxy-N,1-dimethyl-5-oxo-2H-pyrrole-3-carboxamideHCID 69655739HCID 69655739, compound2×

Product 1

HCID 546917602-{4-[(3,4-Dichloro-benzyl)-methyl-carbamoyl]-3-hydroxy-2-oxo-2,5-dihydro-pyrrol-1-yl}-succinamic acidYield 6%

Procedure

3-[(3,4-Dichloro-benzyl-methyl-carbamoyl]-2-hydroxy-acrylic acid methyl ester (Compound 12-B) was treated with paraformaldehyde and asparagine 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 a white powder (12 mg, 6% yield). 1H NMR (300 MHz, DMSO) δ: 13.1 (bs, 1H), 11.05 (bs, 1H), 7.62 (d, 1H, J=8.42), 7.53 (s, 1H), 7.51 (s, 1H), 7.25 (bs, 1H), 6.97 (s, 1H), 4.90 (m, 1H), 4.58 (s, 2H), 4.07 (s, 2H), 2.96 (s, 3H), 2.73 (m, 2H). HRMS (M−H) calcd for C17H16N3Cl2O6: 428.0416. found: 428.0415.

Workup

  1. 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-fc8a46587321409a9f36b280ff6df6c1
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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