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
Reaction equation
[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]Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 25 °C
Procedure
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
Workup
- 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
Sources & evidence
- ORD record
- ord-57ed2073b45b4d48a7a67f31a2a88f0f
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238655B2
Reaction notes
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