Acrylic Acid → 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic Acid
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][C:8](=[O:22])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3][CH2:2]1.[C:23]([OH:27])(=[O:26])[CH:24]=[CH2:25]>C(Cl)Cl>[C:11]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:8]([O:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:25][CH2:24][C:23]([OH:27])=[O:26])[CH2:6][CH2:5]1)=[O:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A round bottomed flask was charged with biphenyl-2-ylcarbamic acid piperidin-4-yl ester (50 g, 67.6 mmol, 1 equiv.; prepared as described in Preparation 1) and 500 mL of DCM. Acrylic acid (15.05 mL, 100 mmol, 1.3 equiv.) was added and the reaction was heated to 50° C. (reflux) for 18 hours. The DCM was removed in vacuo and MeOH (600 mL) was added. The MeOH solution was heated to 75° C. for 2 hours then allowed to cool to room temperature, during which time a thick slurry formed. The precipitate was collected via vacuum filtration, washed with MeOH (50 mL), and dried on the filter to afford 61 g of the title intermediate (98% yield).
Workup
- temperature(reflux) for 18 hours
- customThe DCM was removed in vacuo and MeOH (600 mL)
- additionwas added
- temperatureThe MeOH solution was heated to 75° C. for 2 hours
- temperatureto cool to room temperature, during which time a thick slurry
- customformed
- filtrationThe precipitate was collected via vacuum filtration
- washwashed with MeOH (50 mL)
- customdried on the
- filtrationfilter
Sources & evidence
- ORD record
- ord-f88e1672086a49a2b0f16307f348a82d
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07642355B2
Reaction notes
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