Sodium Hydroxide → HCID 66891968, compound

HRID 2381501Notes

Reaction equation

HRID 2381501 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([N:11]1[N:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>CO>[CH:6]1([CH2:5][CH:4]([N:11]2[N:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[C:3]([OH:22])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668940223-cyclopentyl-2-(1-oxo-1H-phthalazin-2-yl)-propionic acid methyl ester

Product 1

HCID 66891968HCID 66891968, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(1-oxo-1H-phthalazin-2-yl)-propionic acid methyl ester (1.76 g, 5.85 mmol) in methanol (3.9 mL, 1.5M) was treated with a 4N aqueous sodium hydroxide solution (1.61 mL, 6.44 mmol) and stirred at 25° C. for 4 h. At this time, the reaction was concentrated in vacuo. The residue was diluted with water (100 mL) and was acidified with a 2N aqueous hydrochloric acid solution and then extracted with a solution of 90/10 methylene chloride/methanol (3×100 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(1-oxo-1H-phthalazin-2-yl)-propionic acid (1.58 g, 94%) as a white solid; ES+-HRMS m/e calcd for C16H18N2O3 [M+H+] 287.1390, found 287.1390.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. additionThe residue was diluted with water (100 mL)
  3. extractionextracted with a solution of 90/10 methylene chloride/methanol (3×100 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-99330e7e110c4ffcb49850c99e9d7fec
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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