Ethanol → N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-beta-alanine
Reaction equation
[Li+].[OH-].C([O:5][C:6](=[O:35])[CH2:7][CH2:8][NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:34])/[CH:19]=[CH:20]/[CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH2:13]1)=[O:11])C.O1CCCC1.C(O)C>O>[C:30]([O:29][C:27]([N:24]1[CH2:23][CH2:22][CH:21](/[CH:20]=[CH:19]/[C:18]([N:14]2[CH2:15][CH2:16][CH2:17][C@@H:12]([C:10]([NH:9][CH2:8][CH2:7][C:6]([OH:35])=[O:5])=[O:11])[CH2:13]2)=[O:34])[CH2:26][CH2:25]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of LiOH (0.18 g) in water (10 ml) was added to a solution of N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine ethyl ester (1.74 g) in the mixture of tetrahydrofuran (10 ml) and ethanol (10 ml) at 0° C. The reaction mixture was stirred for overnight at room temperature, and the solvent was evaporated in vacuo. The residue was resolved in ethyl acetate-water, and acidified with 10% aqueous KHSO4. The whole was washed with water, brine, dried over MgSO4, and evaporated in vacuo to give N-[(R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidylcarbonyl]-β-alanine as a colorless oil (1.64 g).
Workup
- customthe solvent was evaporated in vacuo
- washThe whole was washed with water, brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-dafcb7c7afb54eda93b8893abc13f878
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384028B1
Reaction notes
Loading…