Trifluoroacetic anhydride → HCID 178525195, compound
Reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:14]([C:17]1[CH:37]=[CH:36][C:20]([CH2:21][O:22][C:23]([N:25]2[CH2:30][CH2:29][N:28]([N:31]=O)[CH:27]([C:33]([OH:35])=[O:34])[CH2:26]2)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]>C1COCC1>[N+:14]([C:17]1[CH:37]=[CH:36][C:20]([CH2:21][O:22][C:23]([N:25]2[CH2:30][CH2:29][N+:28]3[C-:27]([C:33](=[O:35])[O:34][N:31]=3)[CH2:26]2)=[O:24])=[CH:19][CH:18]=1)([O-:16])=[O:15]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The THF (10 mL) solution of trifluoroacetic anhydride (24.0 g) was added to the THF (371 mL) solution of crude 4-nitrosopiperazine-1,3-dicarboxylic acid 1-(4-nitrobenzyl) ester under a nitrogen atmosphere at 0° C. for 15 min. The solution was stirred for 1.5 h at 0° C. and for 1 h at room temperature. The THF (5 mL) solution of trifluoroacetic anhydride (8.0 g) was added to the solution for 5 min and stirred for 20 h at room temperature. To the solution was added trifluoroacetic anhydride (8.0 g) for 5 min and the solution was stirred for 4 h. The precipitate was filtered and washed with THF and Et2O. The filtrate was concentrated under reduced pressure. The residue was triturated with THF, filtered and washed with Et2O. These materials were combined and dried under reduced pressure to afford the titled compound as colorless crystals (22.3 g, 91%).
Workup
- stirringstirred for 20 h at room temperature
- stirringthe solution was stirred for 4 h
- filtrationThe precipitate was filtered
- washwashed with THF and Et2O
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was triturated with THF
- filtrationfiltered
- washwashed with Et2O
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-50aa3c3640b74cc7a213bff40dc92ff6
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112582B2
Reaction notes
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