Pyridine → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate
Reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][O:17][C:18](=[O:36])[C@H:19]([CH2:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][CH:30]=1)[NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].N1C=CC=CC=1>ClCCl>[CH3:16][O:17][C:18](=[O:36])[C@@H:19]([NH:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:31][CH:30]=1Participants
5
Procedure
Trifluoromethanesulfonic anhydride (3.27 ml, 19.47 mmol) was slowly added to a solution of Boc-L-tyrosine methyl ester (5.0 g, 16.93 mmol) and pyridine (4.11 ml, 50.79 mmol) in dichloromethane (145 ml) at 0° C. and the resulting orange solution was stirred at room temperature for 4 h. The reaction was quenched by addition of NaHCO3 solution (150 ml) and the organic layer was separated, washed with saturated aqueous NaHCO3 (2×100 ml) and brine (1×100 ml), and dried (MgSO4). The solvent was concentrated under reduced pressure to yield (S)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl) propionic acid methyl ester (6.52 g, 90%) that was used in the next step without further purification.
Workup
- customThe reaction was quenched by addition of NaHCO3 solution (150 ml)
- customthe organic layer was separated
- washwashed with saturated aqueous NaHCO3 (2×100 ml) and brine (1×100 ml)
- dry with materialdried (MgSO4)
- concentrationThe solvent was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-3983fbc31e944919bd4a0e9a3ea2a563
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253171B2
Reaction notes
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