Acetic Anhydride → (4-Chloro-2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}pyridin-3-yl)methyl Acetate

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:19][CH2:18][C:17]3[C:16]4[CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13][C:12]=4[S:11][C:10]=3[C:9]2=[O:22])[C:3]=1[CH2:23][OH:24].C(N(CC)CC)C.[C:32](OC(=O)C)(=[O:34])[CH3:33]>>[C:32]([O:24][CH2:23][C:3]1[C:4]([N:8]2[CH2:19][CH2:18][C:17]3[C:16]4[CH2:15][C:14]([CH3:20])([CH3:21])[CH2:13][C:12]=4[S:11][C:10]=3[C:9]2=[O:22])=[N:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:34])[CH3:33]

参加物

反応物 3

HCID 7918Acetic Anhydride

HCID 8471Triethylamine

HCID 8668459510-[4-Chloro-3-(hydroxymethyl)pyridin-2-yl]-4,4-dimethyl-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-9-one

生成物 1

HCID 86684596(4-Chloro-2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}pyridin-3-yl)methyl Acetate収率 90%

反応条件

温度: 25 °C

実験手順

A mixture of 330a (1.0 g, 2.76 mmol), triethylamine (610 mg, 6.0 mmol), and acetic anhydride (5 mL) was stirred at 25° C. for 2 h. Then the reaction mixture was quenched with water (10 mL) and the pH was adjusted to around 8 with NaHCO3 (aq.). The mixture was extracted with dichloromethane (2×15 mL). The combined dichloromethane extract was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with 1:1 ethyl acetate/petroleum ether to afford 330b as a pale yellow solid (1.0 g, 90%). MS-ESI: [M+H]+ 405.2

後処理

customThen the reaction mixture was quenched with water (10 mL)
extractionThe mixture was extracted with dichloromethane (2×15 mL)
extractionThe combined dichloromethane extract
concentrationwas concentrated under reduced pressure
customthe residue was purified by silica-gel column chromatography
washeluting with 1:1 ethyl acetate/petroleum ether

出典と根拠

ORDレコード: ord-f55286cd1b6d44c0968c231136be778d
出典データセット: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08716274B2

反応ノート

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