Acrylic Acid → 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic Acid

HRID 1097014Notes

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

Conditions

Temperature: 75 °C

Procedure

A stirred solution of biphenyl-2-ylcarbamic acid piperidin-4-yl ester (50.0 g, 168.7 mmol) (see, e.g., U.S. Patent Publication No. 2006/0035931 A1, published Feb. 16, 2006) and acrylic acid (15.1 mL, 219.3 mmol) in DCM (500 mL) was heated at 50° C. overnight. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in MeOH (600 mL). The resulting solution was heated at 75° C. for 2 h and then allowed to stand at room temperature for about 48 h. The resulting solid was collected by filtration, washed with MeOH, and dried to give the title compound (61.5 g, 99% yield).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionthe residue was dissolved in MeOH (600 mL)
filtrationThe resulting solid was collected by filtration
washwashed with MeOH
customdried

Sources & evidence

ORD record: ord-2acb3766e8c841dfa0536dc6fdcca9bf
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138345B2

Reaction notes

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