Trifluoroacetic acid → (R)-3-(ethyldisulfanyl)-2-(methylamino)propanoic acid
Reaction equation
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.[CH2:15]([S:17][S:18][CH2:19][C@H:20]1[C:24](=[O:25])[O:23][CH2:22][N:21]1C(OC(C)(C)C)=O)[CH3:16]>ClCCl>[CH2:15]([S:17][S:18][CH2:19][C@H:20]([NH:21][CH3:22])[C:24]([OH:25])=[O:23])[CH3:16]Participants
5
Procedure
Triethylsilane (4.46 ml, 27.9 mmol) and trifluoroacetic acid (6.88 ml, 89.0 mmol) were added to a solution of (R)-tert-butyl 4-((ethyldisulfanyl)methyl)-5-oxooxazolidine-3-carboxylate (Compound 2e-F) (819 mg, 2.79 mmol) in dichloromethane (14 ml) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated under reduced pressure, and the resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40) to afford (R)-3-(ethyldisulfanyl)-2-(methylamino)propanoic acid (Compound 2f-F) (232 mg, 43%).
Workup
- concentrationThe reaction mixture was then concentrated under reduced pressure
- customthe resulting residue was purified by reverse-phase silica gel column chromatography (10 mM aqueous ammonium acetate solution/methanol=100/0→60/40)
Sources & evidence
- ORD record
- ord-399687e5a4a64c709b4d2cca4bfcf184
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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