Acetic Anhydride → HCID 86726800, compound
Reaction equation
[OH:1][C:2]1([CH3:30])[C@@H:7]([CH3:8])[CH2:6][N:5]([C:9]2[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][N+:12]([O-])=[C:11]3[CH2:19][CH2:20][CH2:21][C:10]=23)[CH2:4][C@H:3]1[NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].[CH3:31][C:32]([O:34]C(C)=O)=[O:33]>>[C:32]([O:34][CH:19]1[C:11]2=[N:12][CH:13]=[C:14]([N+:15]([O-:17])=[O:16])[C:9]([N:5]3[CH2:6][C@H:7]([CH3:8])[C:2]([OH:1])([CH3:30])[C@H:3]([NH:22][C:23]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:29])[CH2:4]3)=[C:10]2[CH2:21][CH2:20]1)(=[O:33])[CH3:31]Participants
3
Conditions
- Temperature
- 90 °C
Procedure
A mixture of tert-butyl [(3R,5S)-4-hydroxy-4,5-dimethyl-1-(3-nitro-1-oxido-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (390 mg, 0.92 mmol) and Ac2O (2 mL) was stirred at 90° C. for 1 h. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The mixture was neutralized with aq. NaHCO3 and then extracted with EtOAc. The combined organic extracts were dried and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography eluting with 20-80% EtOAc in hexanes to give the desired product as a yellow oil (196 mg, 55% in 2 steps). LCMS calc. for C22H33N4O7 (M+H)+ m/z=465.2. found 465.1.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- concentrationconcentrated under reduced pressure
- extractionextracted with EtOAc
- customThe combined organic extracts were dried
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel chromatography
- washeluting with 20-80% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-c432489ca6a7459cbaf9c96bf0be067b
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200004B2
Reaction notes
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