Reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH2:37][CH2:38][S:39][CH3:40])[C:34]([OH:36])=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].CCN(C(C)C)C(C)C.[NH2:50][CH:51]1[CH2:56][CH2:55][N:54]([C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[CH2:53][CH2:52]1.[OH-].[Na+]>CN(C=O)C>[C:25]([O:29][C:30]([NH:32][C@@H:33]([CH2:37][CH2:38][S:39][CH3:40])[C:34]([NH:50][CH:51]1[CH2:52][CH2:53][N:54]([C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)=[O:58])[CH2:55][CH2:56]1)=[O:36])=[O:31])([CH3:26])([CH3:27])[CH3:28]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of HBTU (8.1 g, 21 mmol), (S)-2-(tert-butoxycarbonylamino)-4-(methylthio)butanoic acid (5.3 g, 21 mmol) and DIEA (8.2 mL, 47 mmol) in DMF (50 mL) was stirred at ambient temperature for 30 minutes. Benzyl 4-aminopiperidine-1-carboxylate (5.0 g, 21 mmol) was added and the mixture was stirred at ambient temperature for 18 hours. The mixture was poured into 1N NaOH (500 mL) and the combined organic layers were extracted into EtOAc (500 mL). The combined organic layers were washed with 1N HCl (500 mL) and brine (500 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to yield (S)-benzyl 4-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)piperidine-1-carboxylate (10 g, 21 mmol, 100%).
Workup
- extractionthe combined organic layers were extracted into EtOAc (500 mL)
- washThe combined organic layers were washed with 1N HCl (500 mL) and brine (500 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-03464b571e664c12a611bb3abc3d4c73
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754226B2
Linked notes
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