تفاعل #9178

ord-1345b2679a1f4255af5f660665af3050

معادلة التفاعل

O=C1OCCN1P(=O)(Cl)N1CCOC1=O
bis-(2-oxo-3-oxazolidinyl)-phosphorylchloride
CCN(CC)CC
triethylamine
Cl.NOCc1ccccc1
O-benzylhydroxylamine hydrochloride
O=C(O)CCCCCCCBr
8-bromo octanoic acid
O=C(CCCCCCCBr)NOCc1ccccc1
8-bromo-octanoic acid benzyloxyamide
المردود 78.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGStirring
  2. 2
    استخلاصThe 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. 3
    أخرىThe organic solvent was removed i

الإجراء التجريبي

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+)

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07091229B2uspto-grants-2006_08