1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 21091363, compound

HRID 1349516Notes

Reaction equation

HRID 1349516 reaction equation
[C:1]([O:9][C:10]1[C:11](=[O:40])[N:12]([CH3:39])[CH:13]=[C:14]([CH2:19][CH2:20][O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:15]=1[C:16]([OH:18])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.CCN=C=NCCCN(C)C.[Cl:75][C:76]1[CH:77]=[C:78]([CH:81]=[CH:82][CH:83]=1)[CH2:79][NH2:80]>CN(C)C=O.O>[C:1]([O:9][C:10]1[C:11](=[O:40])[N:12]([CH3:39])[CH:13]=[C:14]([CH2:19][CH2:20][O:21][Si:22]([C:35]([CH3:36])([CH3:38])[CH3:37])([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:15]=1[C:16](=[O:18])[NH:80][CH2:79][C:78]1[CH:81]=[CH:82][CH:83]=[C:76]([Cl:75])[CH:77]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 77802Benzenemethanamine, 3-chloro-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23077533HCID 23077533, compound

Product 1

HCID 21091363HCID 21091363, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-benzoyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-1-methyl-2-oxo-1,2-dihydropyridine-4-carboxylic acid (0.956 g) in dimethylformamide (10 ml) were added 1-hydroxybenzotriazole hydrate (HOBT) (0.395 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, (WSC) (0.495 g) and 3-chlorobenzylamine (0.274 ml) and the mixture was stirred at room temperature for 2 hr. Water was added and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated under,reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2) to give 5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-(3-chlorobenzylcarbamoyl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl benzoate (0.615 g). This compound was dissolved in tetrahydrofuran (20 ml), and acetic acid (0.259 ml) and tetrabutylammonium fluoride (0.474 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=10:1) to give 4-(3-chlorobenzylcarbamoyl)-5-(2-hydroxyethyl)-1-methyl-2-oxo-1,2-dihydropyridin-3-yl benzoate (0.213 g).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under,reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-3555fe2ad5c747a19f449606b7013c8a
Source dataset
uspto-grants-2007_05
Patent number
US07211572B2

Reaction notes

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