Triethylamine → 8-Bromo-octanoic acid benzyloxyamide

HRID 9082

Reaction equation

HRID 9082 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 113364038-Bromo-octanoic acid benzyloxyamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+)

Workup

  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

Sources & evidence

ORD record
ord-1345b2679a1f4255af5f660665af3050
Source dataset
uspto-grants-2006_08
Patent number
US07091229B2

Linked notes

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