2,6-Dimethoxybenzoyl chloride → N-[(1S,2R)-2-Aminocyclopentyl]-2,6-dimethoxybenzamide hydrochloride
Reaction equation
[NH2:1][C@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C:8](=[O:14])OC(C)(C)C.CCN(C(C)C)C(C)C.[CH3:24][O:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:27]=1C([Cl:30])=O>C(Cl)Cl>[ClH:30].[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8](=[O:14])[C:27]1[C:26]([O:25][CH3:24])=[CH:34][CH:33]=[CH:32][C:31]=1[O:35][CH3:36]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl N-[(1R,2S)-2-aminocyclopentyl]carbamate (CAS number 721395-15-9; 0.50 g, 2.50 mmol) in dry DCM (8.3 ml) was added DIPEA (1.3 ml, 7.49 mmol) and 2,6-dimethoxybenzoyl chloride (CAS number 1989-53-3; 0.75 g, 3.74 mmol). The reaction was stirred at room temperature under an atmosphere of nitrogen for 17 hours and then partitioned between DCM and water, filtered through a hydrophobic frit and concentrated in vacuo. This was purified by column chromatography (silica, 50-100% ethyl acetate/petrol). To the resulting solid was then added 1,4-dioxane (2 ml) and HCl in 1,4-dioxane (4M, 2 ml) and the reaction was stirred at room temperature for 2 hours and then concentrated in vacuo, and azeotropically distilled with toluene to afford the title compound.
Workup
- custompartitioned between DCM and water
- filtrationfiltered through a hydrophobic frit
- concentrationconcentrated in vacuo
- customThis was purified by column chromatography (silica, 50-100% ethyl acetate/petrol)
- stirringadded 1,4-dioxane (2 ml) and HCl in 1,4-dioxane (4M, 2 ml) and the reaction was stirred at room temperature for 2 hours
- concentrationconcentrated in vacuo
- distillationazeotropically distilled with toluene
Sources & evidence
- ORD record
- ord-b7a973a4d74d414cacbdbd8d77344478
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156829B2
Reaction notes
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