2,6-Lutidine → HCID 58065847, Verbindung

HRID 1752207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752207
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][C:17](=O)[CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.N1C(C)=CC=CC=1C.Cl.[CH2:36]([O:43][NH2:44])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[CH2:36]([O:43]/[N:44]=[C:17](\[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[CH2:16][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([Br:15])=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][CH:3]=[C:2]([Br:1])[CH:14]=2)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 102312Benzyloxyamine hydrochlorideHCID 58065823HCID 58065823, Verbindung

Produkt 1

HCID 58065847HCID 58065847, VerbindungAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product of Step 1 (17.7 mg, 0.0374 mmol, 1.0 equiv) in THF (400 μL) were added 2,6-lutidine (4.4 μL, 0.0374 mmol, 1.0 equiv), O-benzylhydroxylamine hydrochloride (14.3 mg, 0.0898 mmol, 2.4 equiv) and 4A molecular sieves (15.8 mg). The mixture was stirred for 12 h until TLC indicated complete consumption of starting material. The reaction mixture was quenched with saturated NaHCO3 and extracted 3 times with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography (5-10% EtOAc/Hex) to afford 20.2 mg white solid as product, yield 93.4%. 1H NMR (CDCl3, 400 MHz) δ=4.68 (s, 2H) 5.00 (s, 2H) 5.14 (s, 2H) 6.72 (d, J=8.2 Hz, 2H) 6.94 (t, J=7.3 Hz, 1H) 7.47-7.16 (m, 11H) 8.06 (s, 2H)

Aufarbeitung

  1. customconsumption of starting material
  2. customThe reaction mixture was quenched with saturated NaHCO3
  3. extractionextracted 3 times with dichloromethane
  4. dry with materialThe combined organic extracts were dried with MgSO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customIt was further purified by silica gel chromatography (5-10% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-77574b434a1d4c148aaa23801181d45e
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09162980B2

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