3,3-Dimethylbutylamine → 3-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

HRID 491910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491910
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].[CH2:8]([N:15]([CH:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH3:28])[CH:16]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:17][C:18](O)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:8]([N:15]([CH:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH3:28])[CH:16]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:17][C:18]([NH:5][CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])=[O:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Komponenten

6

Edukt 4

HCID 197093,3-DimethylbutylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 670236463-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid

Produkt 1

HCID 670237123-[Benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-N-(3,3-dimethyl-butyl)-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3,3-dimethyl butylamine (0.6 mL, 4.2 mmol), 3-[benzyl-(1-phenyl-ethyl)-amino]-3-cyclohexyl-propionic acid (1.83 g, 3.8 mmol), HBTU (2.2 g, 5.7 mmol), DIPEA (1.5 mL, 8.6 mmol) and DMF (25 mL) was stirred at room temperature for 14 hours. To the reaction mixture was then added sodium bicarbonate(s) (100 mL) and the desired product was extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water, dried over MgSO4 and concentrated to yield a solid. The solid was purified by column chromatography (10% EtOAc/heptane) to yield a residue.

Aufarbeitung

  1. extractionadded sodium bicarbonate(s) (100 mL) and the desired product was extracted with ethyl acetate (100 mL×2)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto yield a solid
  6. customThe solid was purified by column chromatography (10% EtOAc/heptane)
  7. customto yield a residue

Quellen und Nachweise

ORD-Eintrag
ord-af8bd0aa04bb4220bbd2cfb89723f51d
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

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