Diethylamine → HCID 10503756, Verbindung

HRID 2120899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120899
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(Cl)=O)C(C)C.[CH2:33]([NH:35][CH2:36][CH3:37])[CH3:34]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14]([Br:24])[C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[N:35]([CH2:36][CH3:37])[CH2:33][CH3:34])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 62365Isobutyl chloroformateHCID 10834544HCID 10834544, Verbindung

Produkt 1

HCID 10503756HCID 10503756, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of compound 51 (1.0 g, 2.5 mmol) in dry dichloromethane (10 mL) at −20° C. was added iso-butylchloroformate (450 mg, 3.3 mmol). After 20 min at −20° C. diethylamine (4 mL) was added and the reaction was allowed to warm to room temperature. After 1.5 hrs the solvent was evaporated and the reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate was washed with water and brine and dried over MgSO4 and removed by evaporation. The crude product was purified by silica gel chromatography (0-60% ethyl acetate in heptanes) to give the product (compound 52) as white needles (800 mg, 73%).

Aufarbeitung

  1. customAfter 1.5 hrs the solvent was evaporated
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. washThe ethyl acetate was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customremoved by evaporation
  6. customThe crude product was purified by silica gel chromatography (0-60% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-5c190f40c4c9426f9c298e621f59a706
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693117B2

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