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

HRID 1886261

Reaktionsgleichung

Reaktionsgleichung von HRID 1886261
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a568e0b6f0bc484b8def13e530a361c2
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149859

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