1-Hydroxybenzotriazole → 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide

関与物質

役割	名称	HCID	仕込み量
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
反応物	(R)-1-Phenylpropylamine	HCID 5324978	—
反応物	1H,3H,4H-Pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid	HCID 82597261	—
溶媒	Water	HCID 962	—
溶媒	Dimethylformamide	HCID 6228	—
生成物	3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide	HCID 118946037	59%

反応条件

温度	50 °C

反応手順

To a solution of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid (comp. no. 8a) (5 g, 29.9 mmol) in dimethylformamide (50 ml) was added 1-hydroxybenzotriazole (4.45 g, 32.9 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.31 g, 32.9 mmol). The mixture was stirred for 1 h at 50° C., then (R)-1-phenyl-propylamine (4.45 g, 32.9 mmol) was added and the mixture was stirred at 25° C. overnight. An excess of water was added, the precipitate was filtered off, washed with a small amount of water and dried in vacuo to give 5.05 g (59%) of 3,4-dihydro-1H-pyrrolo[2,1-c][1,4]oxazine-8-carboxylic acid ((R)-1-phenyl-propyl)-amide as a white solid. LC/MS (method 2): Rt=1.05 min; m/z=285.23 (M+H+).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09284333B2
出典データセット	uspto-grants-2016_03
ORD ID	ord-5f5e2214fbdb43c8b9d98ebdb3f8635f
出典メモ	uspto-grants-2016_03