Triethylamine → HCID 60209725, Verbindung

HRID 2264168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264168
[CH3:1][CH:2]([CH3:17])[CH2:3][NH:4][CH2:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][O:28][CH:27]([C:31](O)=[O:32])[CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>ClCCl>[CH2:3]([N:4]([CH2:5][C:6]1[CH:16]=[CH:15][C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:8]=2[CH:7]=1)[C:31]([CH:27]1[O:28][CH2:29][CH2:30][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:26]1)=[O:32])[CH:2]([CH3:17])[CH3:1]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 60209724HCID 60209724, Verbindung

Produkt 1

HCID 60209725HCID 60209725, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.51 g (2.2 mmol) of 2-methyl-N-(2,3,4,5-tetrahydro-1-benzoxepin-8-ylmethyl)propan-1-amine, 0.51 g (2.2 mmol) of (±)-4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (Chem-Impex International), 0.59 g (4.4 mmol) of 1-hydroxybenzotriazole hydrate, 0.84 g (4.4 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.71 mL (5.1 mmol) of triethylamine in 15 mL in dichloromethane was stirred overnight. The mixture was concentrated under reduced pressure, partitioned between 90 mL of ethyl acetate and 30 mL of saturated sodium bicarbonate, and the layers were separated. The organic layer was washed with 30 mL each of water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow oil. Purification by flash chromatography (10-70% ethyl acetate in hexanes) gave 0.84 g (86%) of product as a solid white foam. MS (m+1)=447.4; H NMR (400 MHz, CDCl3) 7.09 (m, 1H), 6.8 (m, 2H), 4.7 (m, 1H), 4.44 (d, 1H, J 17 Hz), 4.2-3.8 (m, 6H), 3.50 (m, 1H), 3.21 (m, 2H), 3.02 (m, 2H), 2.79 (m, 2H), 1.96 (m, 3H), 1.72 (m, 2H), 1.45 (d, 9H, J 13 Hz), 0.85 (m, 6H).

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. custompartitioned between 90 mL of ethyl acetate and 30 mL of saturated sodium bicarbonate
  3. customthe layers were separated
  4. washThe organic layer was washed with 30 mL each of water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow oil
  9. customPurification by flash chromatography (10-70% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-984b49b6b03f430d929677963ee01365
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855201B2

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