Hydrochloric Acid → N-hydroxy-N-(2-naphthylmethyl)-4methoxycarbonylbutanamide

HRID 1886261

Reaction equation

HRID 1886261 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][NH:12][OH:13].C(N(CC)CC)C.[CH3:21][O:22][C:23]([CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])=[O:24].Cl>C1COCC1.O>[OH:13][N:12]([CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:23]([O:22][CH3:21])=[O:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 73917Monomethyl glutarateHCID 15648027N-(naphthalen-2-ylmethyl)hydroxylamine

Product 1

HCID 19877536N-hydroxy-N-(2-naphthylmethyl)-4methoxycarbonylbutanamideYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Into a solution of 52 mg (0.3 mmol) of 2-naphthylmethylhydroxylamine in THF (5 ml) and water (1 ml) was added 30 mg (0.3 mmol) of triethylamine, and then a solution of 49 mg (0.3 mmol) of acid chloride of 4-methoxycarbonylbutanoic acid in THF (1 ml), followed by stirring at room temperature for 30 minutes. 1N-HCl (5 ml) was added and the desired product was extracted with methylene chloride. The extract was successively washed with water, aqueous NaCl, and then dried over anhydrous magnesium sulfate to give a purified product, which was then subjected to silica gel column chromatography to obtain 58 mg (64%) of the desired product.

Workup

  1. extractionthe desired product was extracted with methylene chloride
  2. washThe extract was successively washed with water, aqueous NaCl
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customto give a purified product, which

Sources & evidence

ORD record
ord-a568e0b6f0bc484b8def13e530a361c2
Source dataset
uspto-grants-1992_09
Patent number
US05149859

Linked notes

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