1-Benzylpiperazine → HCID 31765710, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:62]([N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([N:72]1[CH2:73][CH2:74][N:69]([CH2:62][C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH2:70][CH2:71]1)=[O:12])([CH3:2])([CH3:3])[CH3:4]Participants
7
Procedure
(S)-2-tert-Butoxycarbonylamino-3-phenyl-propionic acid (3 g, 11.3 mmol) was dissolved in DMF (100 mL), and PyBOP (5.9 g, 11.3 mmol) and Hünig's base (3.36 g, 25.99 mmol) were added, followed by 1-benzyl-piperazine (2 g, 11.3 mmol). Stirring at rt was continued for 8 h, followed by the addition of EtOAc (400 mL). The mixture was washed with 1 N aq. HCl (300 mL), sat. aq. sodium hydrogencarbonate solution (300 mL) and brine (300 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 4.375 g (91%) of [(S)-1-benzyl-2-(4-benzyl-piperazin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester. LC-MS: tR=0.80 min; [M+H]+=424.34.
Workup
- washThe mixture was washed with 1 N aq. HCl (300 mL), sat. aq. sodium hydrogencarbonate solution (300 mL) and brine (300 mL)
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-9a6baced994c4572916a231f70892208
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067419B2
Reaction notes
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