Sodium Hydroxide → HCID 69358635, compound

HRID 852668Notes

Reaction equation

HRID 852668 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH:5]=1.[OH-].[Na+]>C1COCC1>[CH3:22][N:19]1[CH2:20][CH2:21][N:16]([C:6]2[CH:5]=[C:4]([CH:9]=[C:8]([N:10]3[CH2:14][CH2:13][CH2:12][C:11]3=[O:15])[CH:7]=2)[C:3]([OH:23])=[O:2])[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69358629HCID 69358629, compound

Product 1

HCID 69358635HCID 69358635, compoundYield 138.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 3-(4-methyl-piperazin-1-yl)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (B115) (296 mg, 0.93 mmol, 1 equiv) in THF (10 ml) was added 1N aqueous NaOH solution (1.8 ml, 1.8 mmol, 2 equiv). The resulting mixture was stirred for 14 h then concentrated in vacuo. The residual solid was extracted thoroughly with MeOH and the extracts were concentrated in vacuo to give 3-(4-methyl-piperazin-1-yl)-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid (A115) (390 mg, 138%) as an off white solid. [M+H]+=304.0, RT=1.64 min

Workup

  1. concentrationthen concentrated in vacuo
  2. extractionThe residual solid was extracted thoroughly with MeOH
  3. concentrationthe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-8b2d6c57f8ae4fb6a46b75fbc2be4efe
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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