Isobutyryl chloride → Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate

HRID 62670

Reaktionsgleichung

Reaktionsgleichung von HRID 62670
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>ClCCl.O>[C:21]([NH:1][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14](=[O:20])[O:15][C:16]([CH3:17])([CH3:19])[CH3:18])(=[O:25])[CH:22]([CH3:24])[CH3:23]

Komponenten

5

Edukt 2

HCID 62325Isobutyryl chlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Produkt 1

HCID 71007313Tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate (200 mg, 0.689 mmol) in dichloromethane (4 mL) was added isobutyryl chloride (0.08 mL, 0.76 mmol, 1 equiv.) and TEA (0.23 mL, 1.72 mmol, 2.5 equiv.) at 0° C. The reaction was warmed to room temperature and stirred for 16 h. The reaction was then diluted with dichloromethane and water. The organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The crude material was purified by column chromatography (silica gel, EtOAc/hexanes) to afford tert-butyl (2-isobutyramido-4-(thiophen-2-yl)phenyl)carbamate (0.2 g, 81% yield).

Aufarbeitung

  1. washThe organic layers were washed with water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by column chromatography (silica gel, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-0b625983cee54cefb2c94de1ba51cf0f
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447030B2

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