Dichloromethane → 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chloride

HRID 74823

Reaction equation

HRID 74823 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=O.[Cl:16]CCl>C(Cl)(=O)C(Cl)=O.CN(C=O)C>[O:1]=[C:2]1[CH:6]=[CH:5][C:4](=[O:7])[N:3]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([Cl:16])=[O:15]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 5736836-Maleimidohexanoic acid

Product 1

HCID 114247166-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl chlorideYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 65578Oxalyl chlorideSolvent

Procedure

To a stirring solution of 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid (3.15 g, 14.9 mM) in 15 mL of dichloromethane, oxalyl chloride (1.61 mL, 17.9 mM) was added followed by one drop of DMF. The reaction was allowed to stir at room temperature for three hours. The reaction was concentrated in vacuo. The residue was dissolved in a one to one solution of heptane and dichloromethane and then concentrated in vacuo. This process was repeated two more times producing a solid #248 (3.43 g, 100%). 1H NMR (400 MHz, DMSO-d6): δ [7.02 (s, 2H), 3.43 (m, 2H), 2.53 (m, 1H), CH2.18 (m, 1H), 1.54 (m, 4H), 1.26 (m, 2H).]

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionThe residue was dissolved in a one to one solution of heptane and dichloromethane
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6526d9d97fce432eb40b3e77b6705e27
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Linked notes

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