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

HRID 72112

反応式

[Cl:1][C:2]1[C:3]([OH:12])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C2C(=CC=CC=2)N=CC=1.[N+]1([O-])C2C(=CC=CC=2)[N+]([O-])=CC=1.C(Cl)(=O)C.O[C@@H:40]1[CH2:44][N:43]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:42]([C:52]([O:54][CH3:55])=[O:53])[CH2:41]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[C:3]([O:12][C@H:40]2[CH2:44][N:43]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C@H:42]([C:52]([O:54][CH3:55])=[O:53])[CH2:41]2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

反応条件

温度: 20 °C

実験手順

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)+

後処理

customAfter evaporation of the volatiles
customthe residue was purified on SiO2 (gradient elution, 0-70% EtOAc/petroleum ether)

出典と根拠

ORDレコード: ord-d8e46f6718ea456c8e8983061f4f0371
出典データセット: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08828930B2

反応式

参加物

反応物 7

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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