Trifluoroacetic acid → HCID 68419556, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Br:21])=[C:16]([O:19][CH3:20])[CH:17]=2)[N:12](C(OC(C)(C)C)=O)[C:11]=1[Br:29])[NH:5][C:6](=[O:8])[CH3:7].FC(F)(F)C(O)=O.C(Cl)(Cl)Cl.CO>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:30])[C@H:4]([CH2:9][C:10]1[C:18]2[C:13](=[CH:14][C:15]([Br:21])=[C:16]([O:19][CH3:20])[CH:17]=2)[NH:12][C:11]=1[Br:29])[NH:5][C:6](=[O:8])[CH3:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution containing 18.3 mg (0.03 mmol) of (S)-(+)-N-acetyl-2,6-dibromo-1-t-butoxycarbonyl-5-methoxytryptophan methyl ester (9) dissolved in 3.2 mL of chloroform, 0.8 mL of trifluoroacetic acid was added under ice cooling to prepare a 10% solution. Furthermore, the solution was stirred at room temperature for 12 hours. The reaction solution was charged with chloroform. The organic phase was washed with saturated sodium bicarbonate water. The resulting phase was further washed with a saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain colorless oil. Column chromatography using silica gel as a carrier and a chloroform-methanol (99:1, v/v) mixed solvent as an elution solvent was performed to obtain 10.3 mg (70%) of compound (2).
Workup
- washThe organic phase was washed with saturated sodium bicarbonate water
- washThe resulting phase was further washed with a saturated saline
- dry with materialdried over anhydrous sodium sulfate
- distillationThen, the solvent was distilled off under reduced pressure
- customto obtain colorless oil
Sources & evidence
- ORD record
- ord-15840acadcf449cb86d6bf8952837169
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07659304B2
Reaction notes
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