Diisopropylethylamine → Tert-Butyl 4-(3-(Tert-Butyldisulfanyl)-2-(Isobutoxycarbonylamino)Propanamido)Piperidine-1-Carboxylate
Reaction equation
[C:1]([S:5][S:6][CH2:7][CH:8]([NH:12][C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:9]([OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:53]([N:60]1[CH2:65][CH2:64][CH:63]([NH2:66])[CH2:62][CH2:61]1)([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54]>CN(C=O)C>[C:1]([S:5][S:6][CH2:7][CH:8]([NH:12][C:13]([O:15][CH2:16][CH:17]([CH3:19])[CH3:18])=[O:14])[C:9]([NH:66][CH:63]1[CH2:62][CH2:61][N:60]([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:65][CH2:64]1)=[O:11])([CH3:2])([CH3:3])[CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To the acid from Example 59 (6.98 g, 22.6 mmol) in DMF (50 ml was added HATU (8.58 g, 22.6 mmol). After 30 min, Hunig base (4.71 ml, 27.1 mmol) and 1-Boc-4-amino piperidine (5.43 g, 27.1 mmol) were added to the mixture. The reaction was continued stirring at RT for another 3 h. DMF was removed at high vacuum, the crude residue was dissolved in EtAc (300 ml), washed with H2O (50 ml×3). The title compound was obtained after ISCO purification (5% MeOH/DCM).
Workup
- customDMF was removed at high vacuum
- dissolutionthe crude residue was dissolved in EtAc (300 ml)
- washwashed with H2O (50 ml×3)
Sources & evidence
- ORD record
- ord-42028ecd482a4a6fa8304391e0a2b61f
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278987B2
Reaction notes
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