(4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate → methyl 2-((R)-((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:24][C@H:25]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26]1)[CH2:10][NH:11][C:12](=[O:23])OC1C=CC([N+]([O-])=O)=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:32](C(F)(F)F)=O.[Cl:38][C:39]1[CH:40]=[C:41]([C@@H:45]([C@@H:53]2[CH2:58][CH2:57][CH2:56][NH:55][CH2:54]2)[O:46][CH2:47][CH2:48][NH:49][C:50](=[O:52])[OH:51])[CH:42]=[CH:43][CH:44]=1>>[C:6]([NH:8][C@@H:9]([CH2:24][C@H:25]1[CH2:30][CH2:29][CH2:28][O:27][CH2:26]1)[CH2:10][NH:11][C:12]([N:55]1[CH2:56][CH2:57][CH2:58][C@@H:53]([C@H:45]([C:41]2[CH:42]=[CH:43][CH:44]=[C:39]([Cl:38])[CH:40]=2)[O:46][CH2:47][CH2:48][NH:49][C:50](=[O:51])[O:52][CH3:32])[CH2:54]1)=[O:23])([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]Participants
3
Reactant 2
Product 1
Procedure
To (4-nitrophenyl) (S)-2-(N-(tert-butoxycarbonyl)amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamate solution (2 mL, 0.013 mmol) was added 2-((R)-(3-chlorophenyl)((R)-piperidin-3-yl)methoxy)ethylcarbamate TFA salt (7.0 mg, 0.016 mmol), followed by excess TEA (0.3 mL). The mixture was stirred for 30 min, then the solvent was removed in vacuo. The resulting oil was purified on preparative HPLC to give methyl 2-((R)—((R)-1-((S)-2-(Boc-amino)-3-((R)-tetrahydro-2H-pyran-3-yl)propylcarbamoyl)piperidin-3-yl)(3-chlorophenyl)methoxy)ethylcarbamate 5 mg, yield 63%. MS ESI +ve m/z 611 (M+H).