Triethylamine → HCID 44403029, Verbindung

HRID 1744058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744058
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][NH:7][C@@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1CN([P+](O[N:35]2N=[N:42][C:37]3C=CC=C[C:36]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.Cl.NCC#N.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C@@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([NH:42][CH2:37][C:36]#[N:35])=[O:11])=[CH:16][CH:17]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2724699PyBOPHCID 11491918Aminoacetonitrile hydrochlorideHCID 28354564HCID 28354564, Verbindung

Produkt 1

HCID 44403029HCID 44403029, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To (2S)-2-[(4-bromobenzyl)amino]-4-methylpentanoic acid (1.343 g, 4.62 mmol), PyBOP (2.65 g, 5.08 mmol), aminoacetonitrile hydrochloride (940 mg, 10.16 mmol) in dry DMF (30 mL) under dry nitrogen was added triethylamine (2.2 mL, 15.71 mmol) dropwise and the reaction was stirred for 4 hours. Aqueous sat. NaHCO3 was added and the product extracted with Et2O (2×), dried on Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 4/6 then 1/1) to afford (2S)-2-[(4-bromobenzyl)amino]-N-(cyanomethyl)-4-methylpentanamide.

Aufarbeitung

  1. extractionthe product extracted with Et2O (2×)
  2. customdried on Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography over silica gel (EtOAc/Hex, 4/6

Quellen und Nachweise

ORD-Eintrag
ord-4dd1855f5c474c04bcd416d3d8a3e911
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012075B2

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