Tetrahydrofuran → HCID 131729236, compound

HRID 1665206Notes

Reaction equation

HRID 1665206 reaction equation
[CH3:1][O:2][N:3]=[CH:4]/[C:5](/[CH3:15])=[CH:6]/[C@@H:7]1[C@@H:9]([C:10]([OH:12])=[O:11])[C:8]1([CH3:14])[CH3:13].[O:16]1[CH2:20][CH2:19]CC1.Cl.[CH2:22]([N:24]=[C:25]=[N:26][CH2:27][CH2:28][CH2:29]N(C)C)C.[Cl-].[Na+].[OH2:35]>CN(C)C1C=CN=CC=1>[CH3:1][O:2][N:3]=[CH:4]/[C:5](/[CH3:15])=[CH:6]/[C@@H:7]1[C@@H:9]([C:10]([O:12][CH2:22][N:24]2[C:20](=[O:16])[CH2:19][N:26]([CH2:27][C:28]#[CH:29])[C:25]2=[O:35])=[O:11])[C:8]1([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57417360Sodium chloride; waterHCID 86634961HCID 86634961, compound

Product 1

HCID 131729236HCID 131729236, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

0.32 g of (1R)-trans-3-[(E)-3-methoxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid, catalytic amount of 4-dimethylaminopyridine and 5 ml of anhydrous tetrahydrofuran was added 0.30 g of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and the mixture was stirred at room temperature overnight. Thereafter, saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, then, filtrated, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.34 g of 2,5-dioxo-3-(2-propynyl)imidazolidin-1-ylmethyl (1R)-trans-3-[(E)-3-methoxyimino-2-methyl-1-propenyl]-2,2-dimethylcyclopropanecarboxylate (hereinafter, referred to as the present compound (1)) represented by the formula (1):

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcd6405489354f37918e599f96e486f4
Source dataset
uspto-grants-2011_10
Patent number
US08039499B2

Reaction notes

Loading…