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

HRID 1174648Notes

Reaction equation

HRID 1174648 reaction equation
[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]([O:21]C)=[O:20])[CH2:13][CH2:12]1)=[O:9].[OH-].[Li+].O1CCCC1.Cl>O>[C:1]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:15][CH2:16]1)=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57459436Methyl 3-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionate

Product 1

HCID 218806073-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic AcidYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of the product of Step (a) (902 mg, 2.37 mmol) and lithium hydroxide (171 mg, 7.11 mmol) in a 50% mixture of tetrahydrofuran (12 mL) and water (12 mL) was heated at 30° C. overnight and then acidified with concentrated hydrochloric acid. The resulting mixture was lyophilized to give the title compound (˜100% yield, containing some lithium chloride).

Sources & evidence

ORD record
ord-9d764651291b4f9e807394ce95e012c7
Source dataset
uspto-grants-2010_11
Patent number
US07838535B2

Reaction notes

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