Veratrylamine → 1,1-Dimethylethyl 4-[{4-(benzyloxy)-2-[(3,4-dimethoxybenzyl)carbamoyl]phenyl}(isobutoxycarbonyl)amino]piperidine-1-carboxylate

HRID 80463

Reaktionsgleichung

Reaktionsgleichung von HRID 80463
[Na].[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:19]([CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]2)[C:20]([O:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[O:21])=[C:14]([CH:18]=1)[C:15](O)=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:73]([NH2:84])[C:74]1[CH:83]=[CH:82][C:79]([O:80][CH3:81])=[C:76]([O:77][CH3:78])[CH:75]=1>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:11]=[CH:12][C:13]([N:19]([C:20]([O:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[O:21])[CH:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])[CH2:29][CH2:28]2)=[C:14]([C:15](=[O:16])[NH:84][CH2:73][C:74]2[CH:83]=[CH:82][C:79]([O:80][CH3:81])=[C:76]([O:77][CH3:78])[CH:75]=2)[CH:18]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

7

Edukt 5

HCID 79832VeratrylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5360545SodiumHCID 595871175-(Benzyloxy)-2-({1-[(1,1-dimethylethoxy)carbonyl]piperidin-4-yl}[(2-methylpropoxy)carbonyl]amino)benzoic acid

Produkt 1

HCID 666037821,1-Dimethylethyl 4-[{4-(benzyloxy)-2-[(3,4-dimethoxybenzyl)carbamoyl]phenyl}(isobutoxycarbonyl)amino]piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 6 g of sodium salt of 5-(benzyloxy)-2-({1-[(1,1-dimethylethoxy)carbonyl]piperidin-4-yl}[(2-methylpropoxy)carbonyl]amino)benzoic acid obtained in stage 1.3 and 4.42 g of DIEA in 250 ml of DMF is stirred at AT for 15 min. 6.48 g of HBTU are added and the mixture is left stirring for 30 min. 2.48 g of veratrylamine are added and the reaction mixture is stirred for 48 h 00. It is evaporated under reduced pressure, the residue is taken up in AcOEt, washed with a saturated NH4Cl solution and with a saturated NaHCO3 solution, dried over Na2SO4 and filtered, and the solvent is evaporated under reduced pressure. The residue is chromatographed on silica gel, elution being carried out with an AcOEt/heptane mixture, (20/80, v/v) as far as (60/40, v/v), to give 7.5 g of expected product.

Aufarbeitung

  1. waitthe mixture is left
  2. stirringstirring for 30 min
  3. stirringthe reaction mixture is stirred for 48 h 00
  4. customIt is evaporated under reduced pressure
  5. washwashed with a saturated NH4Cl solution and with a saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent is evaporated under reduced pressure
  9. customThe residue is chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-ef7fdc0c79504a6f83b11d3ddad648fd
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846654B2

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