Reaktion #1605752

ord-b6fff80a1c974dc6b7100131c6f71153

Reaktionsgleichung

Oc1cccc2[nH]nnc12
Hydroxybenzotriazole
CC1CCCC(N)C1C
2,3-dimethylcyclohexanamine
N=C=N
Carbodiimide
NC(CO)(CO)CO
Trisamine
O=C(O)c1ccc2c(c1)OCO2
benzo[d][1,3]dioxole-5-carboxylic acid
CC1CCCC(NC(=O)c2ccc3c(c2)OCO3)C1C
N-(2,3-dimethylcyclohexyl)benzo[d][1,3]dioxole-5-carboxamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas added into the reaction well
  2. 2
    workup.WAITto shake overnight at room temperature
  3. 3
    SonstigeThe solution was evaporated

Vorschrift

2,3-dimethylcyclohexanamine (20 μmol) and benzo[d][1,3]dioxole-5-carboxylic acid (1.1 eq) were each dissolved in acetonitrile/dichloromethane (200 μL, 2:1). PS-Carbodiimide resin (2 eq) was loaded into a 1.2 mL 96 well Greiner plate, followed by the addition of amine and acid solutions. Hydroxybenzotriazole (1.1 eq) was dissolved in DMF (100 mL) and was added into the reaction well. The reaction was shaken overnight at room temperature. Once the reaction was completed, PS-Trisamine resin (1.5 eq) was added into the reaction mixture and the solution was allowed to shake overnight at room temperature. Acetonitrile (200 mL) was added into the reaction well, and the top clear solution was transferred into a new plate. The solution was evaporated to give N-(2,3-dimethylcyclohexyl)benzo[d][1,3]dioxole-5-carboxamide. MS (M+H, 276.20).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09072313B2uspto-grants-2015_07