Water → Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoate

HRID 852525Notes

Reaction equation

HRID 852525 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:16])[CH2:12][CH2:13][CH2:14]Cl)[CH:7]=[C:6]([Br:17])[CH:5]=1.[H-].[Na+].O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:16])[CH:7]=[C:6]([Br:17])[CH:5]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 693569393-Bromo-5-(4-chloro-butanoylamino)-benzoic acid methyl ester

Product 1

HCID 22253055Methyl 3-bromo-5-(2-oxopyrrolidin-1-yl)benzoateYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-5-(4-chloro-butanoylamino)-benzoic acid methyl ester (D13) (530 mg, 1.6 mmol, 1 equiv) in THF (5 ml) at room temperature was added NaH (60% in mineral oil, 64 mg, 1.7 mmol, 1.1 equiv) and the resulting mixture was stirred at room temperature for 2 h. H2O was then added and the resulting mixture was diluted with AcOEt. The two layers were separated and the organic phase dried over MgSO4 and concentrated in vacuo to give 3-bromo-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester (D9a) (361 mg, 76%) as a yellow solid. [M−H]-296.3, RT=2.49.

Workup

  1. customThe two layers were separated
  2. dry with materialthe organic phase dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72188b3811df4aa691a25f135103fa67
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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