Triethylamine → 7-Bromo-heptanoic acid benzyloxyamide

HRID 1636071Notes

Reaction equation

HRID 1636071 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][C:25](O)=[O:26].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1>ClCCl>[CH2:9]([O:16][NH:17][C:25](=[O:26])[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 1217237-Bromoheptanoic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

Product 1

HCID 865865457-Bromo-heptanoic acid benzyloxyamideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an ice bath, 2.4 ml triethylamine was added to a suspension of 2.7 g (17 mmol) O-benzylhydroxylamine hydrochloride in 100 ml dichloromethane. 3.6 g (17 mmol)7-bromo heptanoic acid was added, followed by 5.3 g (21 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. and the residue was purified by column chromatography (silica gel; ethyl acetate: heptane 1:1) to give 1.55 g (30%) of 7-bromo-heptanoic acid benzyloxy-amide as a colorless oil. MS: 314 (M+H+).

Workup

  1. 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
  2. customThe organic solvent was removed i
  3. customand the residue was purified by column chromatography (silica gel; ethyl acetate: heptane 1:1)

Sources & evidence

ORD record
ord-c031ab3530a6464989173dec0dfe62c1
Source dataset
uspto-grants-2003_01
Patent number
US06512123B2

Reaction notes

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