Benzyloxyamine hydrochloride → (2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide

HRID 1786111Notes

Reaction equation

HRID 1786111 reaction equation
[OH:1][CH2:2][C@@H:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:4]([OH:6])=O.Cl.[CH2:14]([O:21][NH2:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[OH:1][CH2:2][C@@H:3]([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])[C:4]([NH:22][O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]

Participants

6

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86760836(2R)-2-(Hydroxymethyl)-7-octenoic acid

Product 1

HCID 86621280(2R)-2-(hydroxymethyl)-N-benzoxy-7-octenamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2R)-2-(hydroxymethyl)-7-octenoic acid (1.12 g, 6.51 mmol), O-benzyl hydroxylamine hydrochloride (1.04 g, 6.51 mmol) and 4-dimethylamino-pyridine (1.90 g, 15.62 mmol) in dichloromethane (30 mL) at 0° C. was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.50 g, 7.81 mmol). After stirring at room temperature overnight, the reaction was then quenched with 1N aqueous HCl solution (25 mL) and extracted using dichloromethane (25 mL×2). The organic extracts were washed with water, brine, and dried over MgSO4. Removal of the solvent under reduced pressure yielded the title compound. MH+278.

Workup

  1. customthe reaction was then quenched with 1N aqueous HCl solution (25 mL)
  2. extractionextracted
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-54a5d85e4adc4e3b924e02dda9e1f326
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

Loading…