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O-Methylhydroxylamine hydrochloride → 5-({{3-[(methoxyimino)methyl]benzyl}[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic Acid

HRID 2307693
Notes
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Reaction equation

HRID 2307693 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][N:7]([C@@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)[C:8]([C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]([C:19]([OH:21])=[O:20])=[CH:12][C:11]=1[C:22]([OH:24])=[O:23])=[O:9])=O.Cl.[CH3:39][O:40][NH2:41]>N1C=CC=CC=1>[CH3:39][O:40][N:41]=[CH:1][C:3]1[CH:4]=[C:5]([CH:35]=[CH:36][CH:37]=1)[CH2:6][N:7]([C@@H:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:28][CH2:27][CH2:26]1)[C:8]([C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[C:13]([C:19]([OH:21])=[O:20])=[CH:12][C:11]=1[C:22]([OH:24])=[O:23])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 102288355-({(3-formylbenzyl)[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic Acid

Product 1

HCID 865864555-({{3-[(methoxyimino)methyl]benzyl}[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino}carbonyl)-1,2,4-benzenetricarboxylic AcidYield 31.2%

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent

Procedure

The product from Example 76E (132 mg, 0.26 mmol) in pyridine (5 mL) was treated with O-methylhydroxylamine hydrochloride (26 mg, 0.32 mmol). After stirring for 1 hour at room temperature, the volatiles were evaporated under reduced pressure. The residue was dissolved in ethyl acetate and washed with 1N HCl, water, brine, dried (Na2SO4), filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 100:1:1 ethyl acetate:formic acid:water) to provide the title compound as a white solid (43 mg, 31%).

Workup

  1. customthe volatiles were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 1N HCl, water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 100:1:1 ethyl acetate:formic acid:water)

Sources & evidence

ORD record
ord-37525036729e4cbea41e9dabd19dafab
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831193B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes