Water → (R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol

HRID 622376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622376
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:11])[CH3:10])[C:4]=1[OH:12].O.C(=O)(O)[O-].[Na+].[Br:19][C@H:20]([CH:24]([CH3:26])[CH3:25])[C:21](Cl)=[O:22]>C(OCC)(=O)C>[Br:19][C@H:20]([CH:24]([CH3:26])[CH3:25])[C:21]([NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH:9]([CH3:10])[CH3:11])[C:4]=1[OH:12])=[O:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 212930372-Amino-6-isopropylphenol hydrochlorideHCID 22839824(R)-2-bromo-3methylbutyryl chloride

Produkt 1

HCID 6932486(R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenolAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a stirred, ice-cooled mixture of 2-amino-6-isopropylphenol hydrochloride (15.0 g), ethyl acetate (200 ml), water (100 ml), and sodium bicarbonate (20.0 g), was added dropwise a solution of (R)-2-bromo-3methylbutyryl chloride (16.0 g) in ethyl acetate (30 ml). The whole was stirred for 30 minutes, and the ethyl acetate layer was separated, washed with water and dried over MgSO4. Removal of the solvent gave (R)-2-(2-bromo-3-methylbutyryl)amino-6-isopropylphenol as crystals (19.1 g, 76.1%). Recrystallization from isopropyl ether afforded colorless needles, mp 108°-109° C. [α]D23 +44.8° (c=0.82, MeOH).

Aufarbeitung

  1. temperatureTo a stirred, ice-cooled
  2. customthe ethyl acetate layer was separated
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2f24d0c71b41437d93d6c3ff70833fcb
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771050

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