Formaldehyde → methyl 4-[[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]methyl]benzoate

HRID 2214538Notes

Reaction equation

HRID 2214538 reaction equation
Cl[C:2]1C=C(C=CC=1Cl)CN(C)C(=O)C=C1C(=O)OC(C)(C)O1.C=O.Cl.[NH2:26][CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][CH:29]=1.C(N(CC)CC)C.[Cl:44][C:45]1[CH:46]=[C:47]([CH:70]=[CH:71][C:72]=1[Cl:73])[CH2:48][N:49]([CH3:69])[C:50]([C:52]1[CH2:56]N(CCC(NCCC(O)=O)=O)[C:54](=[O:67])[C:53]=1[OH:68])=[O:51]>>[CH3:2][O:33][C:32](=[O:34])[C:31]1[CH:30]=[CH:29][C:28]([CH2:27][N:26]2[CH2:56][C:52]([C:50](=[O:51])[N:49]([CH2:48][C:47]3[CH:70]=[CH:71][C:72]([Cl:73])=[C:45]([Cl:44])[CH:46]=3)[CH3:69])=[C:53]([OH:68])[C:54]2=[O:67])=[CH:36][CH:35]=1

Participants

6

Reactant 5

HCID 712FormaldehydeHCID 8471TriethylamineHCID 105553Benzoic acid, 4-(aminomethyl)-, hydrochloride (1:1)HCID 546917263-[3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoylamino]propanoic acidHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide2×

Product 1

HCID 54698210methyl 4-[[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]methyl]benzoateYield 26%

Procedure

N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide (Compound 37-A) was treated with paraformaldehyde and 4-(aminomethyl)-benzoate hydrochloride salt with 1 equivalent of triethyl amine as described in the preparation of Compound 37. The title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA) to yield the title compound as a yellow foam (0.060 g, 26% yield). 1H NMR (300 MHz, CDCl3) δ: 2.98 (s, 3H), 3.91 (s, 3H), 4.05 (s, 2H), 4.56 (s, 2H), 7.07 (dd, J=1.8 Hz, J=8.1 Hz, 1H), 7.30 (m, 3H), 7.40 (m, 1H), 8.00 (d, J=8.1 Hz, 1H). HRMS (M−H) calcd for C22H20N2Cl2O5: 461.0671. found: 461.0690.

Workup

  1. customThe title compound was purified by chromatography (YMC Combiprep ODS-A, 30 mm×50 mm, MeOH/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-79a6817598264c5b9748061ea0849020
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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