Acetyl chloride → 1-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate

関与物質

役割	名称	HCID	仕込み量
反応物	Acetyl chloride	HCID 6367	—
反応物	Quinoxaline	HCID 7045	—
反応物	Triphenylphosphine	HCID 11776	—
反応物	3-chloro-1H-quinoxalin-2-one	HCID 302705	—
反応物	Diisopropyl azodicarboxylate	HCID 5363146	—
反応物	N-Boc-cis-4-hydroxy-L-proline methyl ester	HCID 10752873	—
反応物	HCID 178526279	HCID 178526279	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	1-t-Butyl 2-methyl (2S,4R)-4-[(3-chloroquinoxalin-2-yl)oxy]pyrrolidine-1,2-dicarboxylate	HCID 58091419	77%

反応条件

温度	20 °C

反応手順

A solution of 3-chloroquinoxalin-2-ol (1.44 g, 7.97 mmol) (Yusuf Ahmad et al., Quinoxaline Derivatives, XI. The Reaction of Quinoxaline 1,4-Dioxide and Some of Its Derivatives with Acetyl Chloride, 38(12) J. ORG. CHEM. 2176 (1973)) and 1-tert-butyl 2-methyl (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate (2.05 g, 8.37 mmol) in THF (190 ml) was cooled to 0° C., then treated with PPh3 (2.51 g, 9.57 mmol). DIAD (1.86 ml, 9.57 mmol) was added dropwise, and the mixture was stirred at 20° C. for 1 hour. After evaporation of the volatiles, the residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether) to afford the title compound (2.5 g, 77%). LCMS (ES+) m/z 408 (M+H)+

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08828930B2
出典データセット	uspto-grants-2014_09
ORD ID	ord-d8e46f6718ea456c8e8983061f4f0371
出典メモ	uspto-grants-2014_09