Triethylamine → 8-Bromo-octanoic acid benzyloxyamide

HRID 9082

Reaktionsgleichung

Reaktionsgleichung von HRID 9082
C(N(CC)CC)C.Cl.[CH2:9]([O:16][NH2:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26](O)=[O:27].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[CH2:9]([O:16][NH:17][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][Br:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 102312Benzyloxyamine hydrochlorideHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 5482758-Bromooctanoic acid

Produkt 1

HCID 113364038-Bromo-octanoic acid benzyloxyamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In an ice bath, 14 ml triethylamine was added to a suspension of 3.2 g (20 mmol) O-benzylhydroxylamine hydrochloride in 150 ml dichloromethane. Stirring was continued until the solution became clear. Then, 4.5 g (20 mmol) 8-bromo octanoic acid was added, followed by 5.6 g (22 mmol) bis-(2-oxo-3-oxazolidinyl)-phosphorylchloride. Stirring was continued at ambient temperature for 18 h. The solution was extracted twice with 150 ml each of 1M aqueous hydrochloric acid and twice with 150 ml each of 1M aqueous sodium bicarbonate. The organic solvent was removed i. vac. to give 5.1 g (78%) of 8-bromo-octanoic acid benzyloxyamide as a colorless oil. MS: 330 (M+H+)

Aufarbeitung

  1. stirringStirring
  2. extractionThe solution was extracted twice with 150 ml each of 1M aqueous hydrochloric acid and twice with 150 ml each of 1M aqueous sodium bicarbonate
  3. customThe organic solvent was removed i

Quellen und Nachweise

ORD-Eintrag
ord-1345b2679a1f4255af5f660665af3050
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091229B2

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