Triethylamine → (S)-N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide

HRID 1039019

Reaktionsgleichung

Reaktionsgleichung von HRID 1039019
[F:1][C:2]([F:13])([F:12])[C:3]([NH:5][C@@H:6]([CH2:10][CH3:11])[C:7]([OH:9])=O)=[O:4].O.O[N:16]1[C:20]2C=[CH:22][CH:23]=[CH:24][C:19]=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.C(N)CCC#C>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:20]([NH:16][C:7](=[O:9])[C@@H:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:13])[F:12])[CH2:10][CH3:11])[CH2:19][CH2:24][C:23]#[CH:22]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 641001Pent-4-yn-1-amineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 79006992(S)-(+)-2-trifluoroacetylaminobutyric acid

Produkt 1

HCID 86653105(S)-N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 500 mL round bottom flask was charged with 2-(S)-(2,2,2-trifluoroacetylamino)-butyric acid (5.0 g, 0.025 mol), 1-hydroxybenzotriazole hydrate (4.5 g, 0.033 mol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (6.4 g, 0.033 mol), 4-(dimethylamino)pyridine (0.02 g, 0.163 mmol), and dimethylformamide (95 mL). To the resulting mixture was then added triethylamine (10.6 mL, 0.076 mol) and pent-4-yn-1-amine (2.7 g, 0.033 mol). The resulting mixture was stirred at room temperature for 22 h, then concentrated in vacuo to yield a residue which was purified via flash silica gel chromatography (Analogix IF-280, SF65-400 g column, gradient 90:10-40:60 Heptane:EtOAc) to yield (S)—N-(pent-4-ynyl)-2-(2,2,2-trifluoroacetamido)butanamide. 1H NMR (300 MHz, CDCl3) δ4.46-4.53 (m, 1H), 3.32-3.48 (m, 2H), 2.23-2.29 (m, 2H), 2.00 (s, 1H), 1.86-1.98 (m, 2H), 1.71-1.83 (m, 2H), and 0.91-0.98 (m, 3H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customto yield a residue which
  3. customwas purified via flash silica gel chromatography (Analogix IF-280

Quellen und Nachweise

ORD-Eintrag
ord-db1c80815cf14d56ad12a051138d2af7
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552032B2

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