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

HRID 2214534Notes

Reaction equation

HRID 2214534 reaction equation
[CH2:1]=O.[CH2:3]([C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])[CH2:4][NH2:5].[Cl:14][C:15]1[CH:16]=[C:17]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:18][N:19]([CH3:31])[C:20](=[O:30])[CH:21]=[C:22]1[C:26](=[O:27])OC(C)(C)[O:23]1>CO>[Cl:14][C:15]1[CH:16]=[C:17]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:18][N:19]([CH3:31])[C:20]([C:21]1[CH2:1][N:5]([CH2:4][CH2:3][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[O:7])[C:26](=[O:27])[C:22]=1[OH:23])=[O:30]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2634653-(3-Aminopropanoylamino)propanoic acidHCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

Product 1

HCID 546917263-[3-[3-[(3,4-dichlorophenyl)methyl-methyl-carbamoyl]-4-hydroxy-5-oxo-2H-pyrrol-1-yl]propanoylamino]propanoic acidYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of paraformaldehyde (0.015 g, 0.5 mmol) and methanol (1.5 mL) was warmed to 55° C. Added to this mixture was H-β-Ala-β-ala-OH (0.08 g, 0.5 mmol) and the solution was stirred 5 min. N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo[1,3]dioxolane-4-ylidene)-N-methyl-acetamide (0.1715 g, 0.5 mmol) was added and the mixture was stirred at 55° C. for 45 min. The mixture was concentrated and the resulting residue was triturated with ethylacetate and filtered to give the desired product as a white solid (0.0358 g, 16% yield). 1H NMR (300 MHz, DMSO) δ: 2.35 (t, J=6.7 Hz, 4H), 2.96 (s, 3H), 3.32 (m, 2H), 3.57 (m, 2H), 4.02 (s, 2H), 4.57 (s, 2H), 7.23 (d, J=6.6 Hz, 1H), 7.51 (s, 1H), 7.61 (d, J=8.4 Hz, 1H), 8.05 (t, J=10.3 Hz, 1H), 10.97 (s, 1H), 12.19 (s, 1H). HRMS (M+H) calcd for C19H21N3Cl2O6: 456.07292. found: 456.0738.

Workup

  1. additionAdded to this mixture
  2. stirringthe mixture was stirred at 55° C. for 45 min
  3. concentrationThe mixture was concentrated
  4. customthe resulting residue was triturated with ethylacetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-391066440e1f40e9b6d50aa546a87d83
Source dataset
uspto-grants-2006_09
Patent number
US07109186B2

Reaction notes

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