(S)-3-amino-3-methylpiperidine-2,6-dione hydrobromide → HCID 58827262, Verbindung

HRID 448408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 448408
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[C:13]([C:14](O)=[O:15])[C:12]=3[C:20]([OH:22])=O)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Br.[NH2:24][C@@:25]1([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]1=[O:32]>N1C=CC=CC=1>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11]3[CH:19]=[CH:18][CH:17]=[C:13]4[C:12]=3[C:20](=[O:22])[N:24]([C@@:25]3([CH3:33])[CH2:30][CH2:29][C:28](=[O:31])[NH:27][C:26]3=[O:32])[C:14]4=[O:15])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 66643102(S)-3-amino-3-methylpiperidine-2,6-dione hydrobromideHCID 672296193-(Indan-5-ylamino)-phthalic acid

Produkt 1

HCID 58827262HCID 58827262, VerbindungAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 3-(indan-5-ylamino)-phthalic acid (0.62 g, 3.1 mmol) and (3S)-3-amino-3-methyl-piperidine-2,6-dione hydrobromide (0.50 g, 2.1 mmol) in pyridine (10 mL) was heated to reflux for 17 hours. The mixture was cooled and evaporated under vacuum. The residue was dissolved in ethyl acetate (100 mL), washed with dilute aqueous HCl (2×100 mL) and water (2×100 mL), and evaporated. The residue was purified by ISCO silica gel flash chromatography using a hexanes-ethyl acetate gradient, eluting 0.37 g of the product, an orange solid, at 70:30 hexanes-ethyl acetate, in 45% yield: mp 200-202° C.; HPLC, Waters Symmetry C-18, 3.9×150 mm, 5 μm, 1 mL/min, 240 nm, 65/35 (CH3CN/0.1% H3PO4): tR=5.40 (99.54%); 1H NMR (DMSO-d6) δ 1.91 (s, 3H), 2.00-2.08 (m, 3H), 2.54-2.75 (m, 3H), 2.82-2.88 (m, 4H), 7.04-7.31 (m, 5H), 7.55 (t, J=7.8 Hz, 1H), 8.30 (s, 1H), 11.00 (s, 1H); 13C NMR (DMSO-d6) δ 21.0, 25.2, 28.6, 29.2, 31.8, 32.4, 58.5, 110.9, 112.4, 118.7, 120.7, 124.9, 132.2, 136.0, 137.2, 139.9, 143.4, 145.1, 167.8, 169.4, 172.2, 172.3; Anal. calcd for C23H21N3O4: C, 68.47; H, 5.25; N, 10.42. Found: C, 68.25; H, 5.12; N, 10.30.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 17 hours
  3. temperatureThe mixture was cooled
  4. customevaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  6. washwashed with dilute aqueous HCl (2×100 mL) and water (2×100 mL)
  7. customevaporated
  8. customThe residue was purified by ISCO silica gel flash chromatography
  9. washeluting 0.37 g of the product

Quellen und Nachweise

ORD-Eintrag
ord-4ba55c11e5ad4befafc3edd65aecc1ba
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481568B2

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