1,2-Dichloroethane → Propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridone

HRID 1387299Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1387299
[C:1](O)(=[O:4])[CH2:2][CH3:3].C1C=NC2N(O)N=NC=2C=1.[CH3:16][O:17][C:18]1[CH:34]=[CH:33][C:21]([CH2:22][N:23]2[CH:28]=[C:27]([Br:29])[C:26]([CH3:30])=[C:25]([NH2:31])[C:24]2=[O:32])=[CH:20][CH:19]=1.C(Cl)CCl>C(Cl)Cl.CN(C=O)C>[C:1]([NH:31][C:25]1[C:24](=[O:32])[N:23]([CH2:22][C:21]2[CH:33]=[CH:34][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH:28]=[C:27]([Br:29])[C:26]=1[CH3:30])(=[O:4])[CH2:2][CH3:3]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 1032Propionic AcidHCID 181649HOAtHCID 217064931-(4-Methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone

Produkt 1

HCID 86757221Propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridoneAusbeute 44,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(S)-tbutoxycarbonylamino-3-[4′-(1″-tbutoxycarbonyl-1″-methyl)ethyl]benzene]propanoic acid (3.20 g, 7.88 mmol) in methylene chloride (20 ml,) and DMF (5 mL) at 0° C. were added HOAT (1.07 g) and 1-(4-methoxybenzyl)-5-bromo-4-methyl-3-amino-2-pyridone (2.80 g, 8.67 mmol). EDC (1.66 g) and TMP (1.04 mL) were added, and the mixture was stirred coming to rt overnight. The methylene chloride was evaporated and DMF (25 mL) was added. Additional EDC (0.80 ;), HOAT (0.50 g) and TMP (0.5 mL) were added. After 3 hours the mixture was diluted with ethyl acetate, and washed with 1N HCl, aqueous sodium bicarbonate and brine. The organic phase was dried (MgSO4), filtered and evaporated. Chromatography of the residue over silica gel (ethyl acetate/hexane 1/3) gave 1-[2′-(S)-tbutoxycarbonylamino-)′-[4″-(1′″-tbutoxycarbonyl-1′″-methyl)ethyl]benzene]propanoylamino-5-bromo-1-(4-methoxybenzyl)-4-methyl-2-pyridone (2.48 g, 3.49 mmol, 44%).

Aufarbeitung

  1. customThe methylene chloride was evaporated
  2. additionDMF (25 mL) was added
  3. additionAdditional EDC (0.80 ;), HOAT (0.50 g) and TMP (0.5 mL) were added
  4. additionAfter 3 hours the mixture was diluted with ethyl acetate
  5. washwashed with 1N HCl, aqueous sodium bicarbonate and brine
  6. dry with materialThe organic phase was dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-dc1f145301f34aa897b699eee03ed9c5
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06268365B1

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