Diisopropylcarbodiimide → 2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide

HRID 1383736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383736
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][CH:13]([NH2:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[C:16]([N:26]([CH3:34])[C@H:27]([C:31](O)=[O:32])[CH:28]([CH3:30])[CH3:29])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:19]([O:18][C:16]([N:26]([CH:27]([CH:28]([CH3:30])[CH3:29])[C:31]([NH:15][CH:13]([CH3:14])[CH2:12][C:7]1[CH:8]=[CH:9][C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=1)=[O:32])[CH3:34])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

7

Edukt 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 211874322-(3-Tert-butyl-4-hydroxyphenyl)-1-methylethylamine

Produkt 1

HCID 211874312-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 0.31 g (1.50 mmol) of 2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethylamine, 0.40 g (1.50 mmol) of Z-N-Me-Val-OH and 0.30 g (2.25 mmol) of HOBT in DMF (5 ml), 0.35 ml (2.25 mmol) of DIC was added under cooling with ice. After being stirred at room temperature for 2 hours, the reaction mixture was diluted with ethyl acetate and washed successively with saturated aqueous NaHCO3, water and saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=125:1) to give 2-[N-(benzyloxycarbonyl)-N-methylamino]-N-[2-(3-tert-butyl-4-hydroxyphenyl)-1-methylethyl]-3-methylbutanamide in the amount of 0.55 g (81%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. washwashed successively with saturated aqueous NaHCO3, water and saturated brine
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; chloroform:methanol=125:1)

Quellen und Nachweise

ORD-Eintrag
ord-b8c06b385d1d4476a397907547536259
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255285B1

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