Triethylamine → N-hydroxy-N-(1-hydroxy-2-naphthyl)-3-methoxycarbonylpropionamide

HRID 1886256Notes

Reaction equation

HRID 1886256 reaction equation
Cl.[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[NH:13][OH:14].C(N(CC)CC)C.[CH3:22][O:23][C:24]([CH2:26][CH2:27][C:28](O)=[O:29])=[O:25].OS([O-])(=O)=O.[K+]>C1COCC1.O>[OH:14][N:13]([C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[OH:2])[C:28](=[O:29])[CH2:27][CH2:26][C:24]([O:23][CH3:22])=[O:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 77487monoMethyl succinateHCID 516920Potassium bisulfateHCID 856138501-Hydroxy-2-naphthylhydroxylamine hydrochloride

Product 1

HCID 15728700N-hydroxy-N-(1-hydroxy-2-naphthyl)-3-methoxycarbonylpropionamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of a 1.68 g (ca. 7.9 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride in THF (10 ml) and water (2 ml) was added, 1.7 ml (12 mmol) of triethylamine, followed by addition of a solution of 300 mg (2 mmol) of acid chloride of 3-methoxycarbonylpropionic acid in THF (2 ml). The mixture was stirred at room temperature for 30 minutes, the reaction was completed by an addition of aqueous KHSO4, the mixture was extracted with methylene chloride, and the organic layer was dried over anhydrous magnesium sulfate.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-3634899761134e95acdb0cfe8ff757f3
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Reaction notes

Loading…