1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)-2-hydroxy-3-methylbutanamide

HRID 591529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591529
[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH2:15])[CH2:11][O:12][C:8]=2[CH:7]=1.[OH:23][CH:24]([CH:28]([CH3:30])[CH3:29])[C:25](O)=[O:26].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:3]=1[CH2:4][O:5][C:6]1[CH:17]=[CH:16][C:9]2[C@H:10]([CH2:13][CH2:14][NH:15][C:25](=[O:26])[CH:24]([OH:23])[CH:28]([CH3:30])[CH3:29])[CH2:11][O:12][C:8]=2[CH:7]=1

Komponenten

7

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 99823(+-)-2-Hydroxyisovaleric acidHCID 516892Sodium BicarbonateHCID 897679342-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine

Produkt 1

HCID 118656156N-(2-((3S)-6-((2,4-Dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethyl)-2-hydroxy-3-methylbutanamideAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-((3S)-6-((2,4-dichlorobenzyl)oxy)-2,3-dihydro-1-benzofuran-3-yl)ethanamine (33.8 mg) and DMF (dry) (5 mL) were added 2-hydroxy-3-methylbutanoic acid (17.72 mg), EDCI (31.0 mg) and HOBt (27.0 mg). The mixture was stirred at room temperature overnight. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (26.0 mg).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-000be4ddf2bc457da56663ff6f5921ea
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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