Reaction #2358537

ord-a2776b1a25004a5f8e00241d048e3c0e

Reaction equation

CC(CO)NC(=O)c1cccc(C=CCCCC(=O)N(C)C)c1
16
CC(CO)NC(=O)c1cccc(C=CCCCC(=O)N(C)C)c1
3-(5-Dimethylcarbamoyl-pent-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide
CC(CO)NC(=O)c1cccc(CCCCCC(=O)N(C)C)c1
3-(5-dimethylcarbamoyl-pentyl)-N-(2-hydroxy-1-methyl-ethyl)-benzamide
→
CC(CO)NC(=O)c1cccc(C#CCCCC(=O)N(C)C)c1
alkyne
CC(CO)NC(=O)c1cccc(C#CCCCC(=O)N(C)C)c1
3-(5-Dimethylcarbamoyl-pent-1-ynyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide

Reactants

CC(CO)NC(=O)c1cccc(C=CCCCC(=O)N(C)C)c1
16
CC(CO)NC(=O)c1cccc(C=CCCCC(=O)N(C)C)c1
3-(5-Dimethylcarbamoyl-pent-1-enyl)-N-(2-hydroxy-1-methyl-ethyl)benzamide
CC(CO)NC(=O)c1cccc(CCCCCC(=O)N(C)C)c1
3-(5-dimethylcarbamoyl-pentyl)-N-(2-hydroxy-1-methyl-ethyl)-benzamide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherto obtain
  2. 2
    Otherwere separated by reverse-phase HPLC chromatography (20% acetonitrile/80% water 20 min isocratic program) (16, 34 mg)

Procedure

The alkyne 8 (0.100 g, 0.3 mmol) was synthesized by Lindlar catalyzed reduction using method E to obtain a mixture of 16 and 3-(5-dimethylcarbamoyl-pentyl)-N-(2-hydroxy-1-methyl-ethyl)-benzamide (13) which were separated by reverse-phase HPLC chromatography (20% acetonitrile/80% water 20 min isocratic program) (16, 34 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09120723B2uspto-grants-2015_09