Sodium Hydroxide → 5-Methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester

HRID 924601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924601
[CH2:1]([O:3][C:4]([NH:6][NH:7][C:8](=[O:19])[CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=1[CH3:18])=[O:5])[CH3:2].[OH-].[Na+].CS(O[CH2:27][CH2:28][N:29]([O:37][CH3:38])[CH2:30][CH2:31]OS(C)(=O)=O)(=O)=O>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:1]([O:3][C:4]([N:6]1[CH2:31][CH2:30][N:29]([O:37][CH3:38])[CH2:28][CH2:27][N:7]1[C:8](=[O:19])[CH2:9][C:10]1[C:11]([CH3:18])=[CH:12][C:13]([CH3:17])=[CH:14][C:15]=1[CH3:16])=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 71145194N'-[2-(2,4,6-Trimethyl-phenyl)-acetyl]-hydrazinecarboxylic acid ethyl esterHCID 86719909Methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester

Produkt 1

HCID 867199175-Methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To a vigorously stirred suspension of N′-[2-(2,4,6-trimethyl-phenyl)-acetyl]-hydrazinecarboxylic acid ethyl ester (4.22 g, 15.96 mmol) in toluene (80 ml) was added aqueous sodium hydroxide (12 ml, 30% NaOH w/w in water) and tetra-butyl ammonium bromide (160 mg, 0.48 mmol) at room temperature, followed by methanesulfonic acid 2-[(2-methanesulfonyloxy-ethyl)-methoxy-amino]-ethyl ester (4.66 g, 16.00 mmol) dropwise over 15 minutes at 65° C. The reaction mixture was heated at 65° C. for 6.5 hours. After cooling, the layers were separated, the organic phase evaporated, the residue dissolved in ethyl acetate, washed with water, dried over sodium sulfate and concentrated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate/dichloromethane 5:4:1). Yield: 2.6 g of 5-methoxy-2-[2-(2,4,6-trimethyl-phenyl)-acetyl]-[1,2,5]triazepane-1-carboxylic acid ethyl ester (compound P3.1) as a colorless oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe layers were separated
  3. customthe organic phase evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate/dichloromethane 5:4:1)

Quellen und Nachweise

ORD-Eintrag
ord-2990e317e520401c94519301f4422b41
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09282743B2

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