Hydrochloric Acid → 2-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetic acid

HRID 1752255Notes

Reaction equation

HRID 1752255 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([O:23]CC)=[O:22])[C:16]3=[O:26])[CH2:11][CH2:10]2)=[O:8])=[CH:5][CH:4]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][N:17]([CH2:20][C:21]([OH:23])=[O:22])[C:16]3=[O:26])[CH2:11][CH2:10]2)=[O:8])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71212189Ethyl 2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetate

Product 1

HCID 712123312-(3-(4-(4-Methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetic acidYield 130.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(3-(4-(4-methoxybenzoyl)piperidin-1-yl)-2-oxopyrrolidin-1-yl)acetate (727 mg, 1.778 mmol) in ethanol (36 mL) was added a 2 N aqueous NaOH solution (1.8 mL). The mixture was stirred 1 hour at room temperature. The reaction was then neutralized to pH 7 with 1 N HCl. The solvents were removed in vacuo, then azeotroped 3 times with dichloromethane. The light yellow foamy solid was dried under high vacuum to afford the title racemic product (835 mg). MS (ESI) [m/e, (M+H)+]=360.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.89-8.01 (m, 2H), 6.96-7.11 (m, 2H), 3.85 (s, 3H), 3.46-3.68 (m, 2H), 3.13-3.46 (m, 5H), 2.93-3.04 (m, 1H), 2.61-2.84 (m, 1H), 2.30-2.42 (m, 1H), 1.95-2.11 (m, 1H), 1.81-1.95 (m, 1H), 1.64-1.78 (m, 2H), 1.44-1.63 (m, 2H).

Workup

  1. customThe solvents were removed in vacuo
  2. customazeotroped 3 times with dichloromethane
  3. customThe light yellow foamy solid was dried under high vacuum

Sources & evidence

ORD record
ord-fd528e6bfb8d4537a2935e47b335a39e
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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