5-Chloro-1H-indole-2-carboxylic acid → (+/-)-trans-N1-(tert-Butoxycarbonyl)-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamine

HRID 459472Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459472
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=O)=[CH:5]2.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:37]([O:41][C:42]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[NH2:51])=[O:43])([CH3:40])([CH3:39])[CH3:38]>CN(C)C=O>[C:37]([O:41][C:42]([NH:44][C@@H:45]1[CH2:50][CH2:49][CH2:48][CH2:47][C@H:46]1[NH:51][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[O:13])=[O:43])([CH3:40])([CH3:38])[CH3:39]

Komponenten

6

Edukt 4

HCID 826935-Chloro-1H-indole-2-carboxylic acidHCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 68910309(+/-)-trans-N1-(tert-Butoxycarbonyl)-N2-[(5-chloroindol-2-yl)carbonyl]-1,2-cyclohexanediamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Chloroindole-2-carboxylic acid (2.88 g), 1-hydroxybenzotriazole monohydrate (2.08 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.95 g) were added to a solution of (±)-trans-N-tert-butoxycarbonyl-1,2-cyclohexanediamine (3.00 g) in N,N-dimethylformamide (10 ml) at room temperature. After stirring for 3 days, the reaction mixture was concentrated under reduced pressure, and dichloromethane (30 ml), a saturated aqueous solution (150 ml) of sodium hydrogencarbonate and water (150 ml). were added to the residue. After collecting colorless precipitate formed was collected by filtration and dried to obtain the title compound (5.21 g) as a colorless solid.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under reduced pressure, and dichloromethane (30 ml)
  2. additionwere added to the residue
  3. customAfter collecting colorless precipitate
  4. customformed
  5. filtrationwas collected by filtration
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-ddf755cba35c4cd58edaa823723b32e3
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192968B2

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