Hydrochloric Acid → Methyl cis(+/-)-2-acetyl-4-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)-4-oxobutanoate
Reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C[O-].[Na+].Cl[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:18]([O:33][CH3:34])[CH2:17]1)=[O:15].Cl>CO.C(OCC)(=O)C>[C:3]([CH:2]([CH2:13][C:14]([N:16]1[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:32])[C@H:18]([O:33][CH3:34])[CH2:17]1)=[O:15])[C:1]([O:7][CH3:8])=[O:6])(=[O:4])[CH3:5]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl acetoacetate (510 mg, 4.4 mmol) was dissolved in methanol (15 ml). Sodium methoxide (210 mg, 3.9 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. Further, benzyl cis(±)-[1-(chloroacetyl)-3-methoxypiperidin-4-yl]carbamate obtained in Example (188a) was dissolved in methanol (10 ml). The solution was added to the reaction solution, and the mixture was stirred at 70° C. overnight. The reaction solution was diluted with ethyl acetate, neutralized with 1 N hydrochloric acid, washed with brine, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the title compound was obtained. The resulting compound was used for the next reaction without purification.
Workup
- additionThe solution was added to the reaction solution
- stirringthe mixture was stirred at 70° C. overnight
- washwashed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentration under reduced pressure
Sources & evidence
- ORD record
- ord-14d31e4c638748b7958e3e138ec29bb3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
Loading…