Dimethylformamide → N-hydroxy-N-(1-hydroxy-2-naphthyl)-6-methoxycarbonylhexanamide

HRID 1886259Notes

Reaction equation

HRID 1886259 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[O:4].CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[OH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[NH:36][OH:37].C(N(CC)CC)C.OS([O-])(=O)=O.[K+]>C1COCC1.O.C(Cl)Cl>[OH:37][N:36]([C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]=1[OH:25])[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4]

Participants

10

Reactant 6

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 88467Methyl hydrogen heptane-1,7-dioateHCID 516920Potassium bisulfateHCID 856138501-Hydroxy-2-naphthylhydroxylamine hydrochloride

Product 1

HCID 15728702N-hydroxy-N-(1-hydroxy-2-naphthyl)-6-methoxycarbonylhexanamideYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Into a 25 ml methylene chloride solution of 500 mg (2.87 mmol) of 6-methoxycarbonylhexanoic acid and 222 μl (2.87 mmol) of DMF was added 564 μl (6.46 mmol) of oxalyl chloride at 0° C., and the mixture was stirred as such for one hour. The mixture was then added to a solution of 3.17 g (15 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride, 3.1 ml (23 mmol) of triethylamine in THF (25 ml), and water (5 ml), at 0° C., and after stirring at 0° C. for one hour and at room temperature for one hour, the reaction was completed with aqueous KHSO4, and the mixture was extracted with methylene chloride. The organic layer was washed with 4N HCl and with saturated aqueous NaCl, and then dried over anhydrous magnesium sulfate, and after evaporation of the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography to give 738 mg (78%) of the desired product.

Workup

  1. stirringafter stirring at 0° C. for one hour and at room temperature for one hour
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with 4N HCl and with saturated aqueous NaCl
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customafter evaporation of the solvent under a reduced pressure

Sources & evidence

ORD record
ord-199c8b68f33746bbaca7158659228c2f
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

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