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

HRID 2214536

Reaction equation

HRID 2214536 reaction equation
ClC1C=C(C=CC=1Cl)CN(C)C(=O)C=C1C(=O)OC(C)(C)O1.C=O.[CH2:25]([C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[CH2:26][NH2:27].[Cl:35][C:36]1[CH:37]=[C:38]([CH:61]=[CH:62][C:63]=1[Cl:64])[CH2:39][N:40]([CH3:60])[C:41]([C:43]1[CH2:47]N(CCC(NCCC(O)=O)=O)[C:45](=[O:58])[C:44]=1[OH:59])=[O:42]>>[Cl:35][C:36]1[CH:37]=[C:38]([CH:61]=[CH:62][C:63]=1[Cl:64])[CH2:39][N:40]([CH3:60])[C:41]([C:43]1[CH2:47][N:27]([CH2:26][CH2:25][C:28]([NH:30][CH2:31][C:32]([OH:34])=[O:33])=[O:29])[C:45](=[O:58])[C:44]=1[OH:59])=[O:42]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 137672beta-AlanylglycineHCID 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 546917432-[3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoylamino]acetic acidYield 7%

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 H-β-ala-gly-OH 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 an amber powder (0.0158 g, 7% yield). 1H NMR (300 MHz, DMSO) δ: 2.45 (t, J=6.9 Hz, 2H), 2.98 (m, 3H), 3.60 (m, 2H), 3.73 (d, J=5.7 Hz, 2H), 4.06 (s, 2H), 4.57 (s, 2H), 7.23 (d, J=7.2, 1H), 7.65 (d, J=8.4 Hz, 1H), 8.32 (m, 1H), 10.98 (bs, 1H), 12.50 (bs, 1H). HRMS (M−H) calcd for C18H19N3Cl2O6: 442.05727. found: 442.0584.

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-fa3a59adbe0a425aa1b1f21bcbf31cd9
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Linked notes

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