Lithium Hydroxide → (S)-5-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinic acid hydrochloride

HRID 407993Notes

Reaction equation

HRID 407993 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[CH:5]=[C:6]([F:33])[C:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][C@H:18]([O:21][C:22]4[CH:23]=[CH:24][C:25]([C:28]([O:30]C)=[O:29])=[N:26][CH:27]=4)[C:17]3=[O:32])[CH2:12][CH2:11]2)=[N:8][CH:9]=1>C1COCC1>[ClH:3].[Cl:3][C:4]1[CH:5]=[C:6]([F:33])[C:7]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][C@H:18]([O:21][C:22]4[CH:23]=[CH:24][C:25]([C:28]([OH:30])=[O:29])=[N:26][CH:27]=4)[C:17]3=[O:32])[CH2:12][CH2:11]2)=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67469713(S)-methyl 5-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate

Product 1

HCID 67469704(S)-5-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinic acid hydrochlorideYield 147.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous 1 M LiOH (1.5 mL, 1.5 mmol) was added to a solution of (S)-methyl 5-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinate (0.17 g, 0.38 mmol) in THF (2 mL). The mixture was stirred overnight at ambient temperature. The THF was removed under vacuum and the resulting aqueous solution was adjusted to pH 1 via the addition of aqueous 1 M HCl. The resulting solids were collected by filtration and air-dried to afford (S)-5-(1-(1-(5-chloro-3-fluoropyridin-2-yl)piperidin-4-yl)-2-oxopyrrolidin-3-yloxy)picolinic acid hydrochloride (0.13 g, 0.28 mmol, 74%).

Workup

  1. customThe THF was removed under vacuum
  2. additionthe resulting aqueous solution was adjusted to pH 1 via the addition of aqueous 1 M HCl
  3. filtrationThe resulting solids were collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-2398f01d14e64709a061f73588bca8be
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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