Reaction equation
C(O)C.C([Cl:7])(=O)C.[CH2:8]([O:10][C:11]([C@@:13]1([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([O:26][C:27](=[O:37])[C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)[CH2:23][N:22]2C(OC(C)(C)C)=O)=[O:20])[CH2:15][C@H:14]1[CH:16]=[CH2:17])=[O:12])[CH3:9]>CCOC(C)=O>[Cl-:7].[CH2:8]([O:10][C:11]([C@@:13]1([NH:18][C:19]([C@@H:21]2[CH2:25][C@@H:24]([O:26][C:27](=[O:37])[C:28]3[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=3)[CH2:23][NH2+:22]2)=[O:20])[CH2:15][C@H:14]1[CH:16]=[CH2:17])=[O:12])[CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
To a stirring solution of ethanol at 0° C., was added acetyl chloride (5.7 g). The resulting solution was aged for 30 min. (2S,4R)-tert-Butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-(4-nitrobenzoyloxy)pyrrolidine-1-carboxylate (7.5 g) was then added as a solution in EtOAc (30 mL) to the acidic ethanol slurry solution at 10° C. The reaction was allowed to proceed for 1 h at 10° C., warmed to 15° C. for 1 h and then warmed to 20° C. After 16 h, EtOAc (30 mL) was added to the slurry and the resulting slurry was filtered. The cake was rinsed with EtOAc (30 mL) that had been cooled to 0° C. The title compound was placed in a vacuum oven, at 43° C., to remove residual solvent (6.9 g, 100% yield).
Workup
- waitto proceed for 1 h at 10° C.
- temperaturewarmed to 20° C
- waitAfter 16 h
- filtrationthe resulting slurry was filtered
- washThe cake was rinsed with EtOAc (30 mL) that
- temperaturehad been cooled to 0° C
- customwas placed in a vacuum oven, at 43° C.
Sources & evidence
- ORD record
- ord-cb8f5081884f4f4f949f0a0e48acf5ba
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748374B2
Linked notes
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