Trifluoroacetic acid → HCID 58778388, compound
Reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methyl 5-((2S,4S)-1-(tert-butoxycarbonyl)-4-fluoro-2-pyrrolidinylmethoxy)pentanoate (1.09 g, 3.27 mmol) was dissolved in methylene chloride (50 ml). At room temperature, trifluoroacetic acid (10 ml) was added to the resulting solution. The mixture was stirred at the same temperature for 3.5 hours. The residue obtained by distilling off the solvent under reduced pressure was diluted with methylene chloride (50 ml). The solution was basified with 1N NaOH, followed by extraction with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby the title compound (590 mg, 77%) was obtained as a yellow oil (this compound was provided for the subsequent reaction without further purification).
Workup
- customThe residue obtained
- distillationby distilling off the solvent under reduced pressure
- additionwas diluted with methylene chloride (50 ml)
- extractionfollowed by extraction with methylene chloride
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationdistilled under reduced pressure
- customto remove the solvent, whereby the title compound (590 mg, 77%)
- customwas obtained as a yellow oil (this compound
- customwas provided for the subsequent reaction without further purification)
Sources & evidence
- ORD record
- ord-0808868cad7f4657904182285e2dd380
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157487B2
Reaction notes
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