HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Sodium Hydroxide → 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid

HRID 2381492
Notes
Print preview

Reaction equation

HRID 2381492 reaction equation
C[O:2][C:3](=[O:18])[CH:4]([N:11]1[C:16](=[O:17])[CH:15]=[CH:14][CH:13]=[N:12]1)[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[C:16](=[O:17])[CH:15]=[CH:14][CH:13]=[N:12]2)[C:3]([OH:18])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668752413-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester

Product 1

HCID 668753533-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acidYield 86.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (2.99 g, 11.97 mmol) in methanol (7.9 mL, 1.5M) was treated with a 4N aqueous sodium hydroxide solution (3.29 mL, 13.16 mmol) and stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. The residue was partitioned between water (100 mL) which was acidified with a 2N aqueous hydrochloric acid solution and a solution of 90/10 methylene chloride/methanol (3×75 mL). The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-cyclopentyl-2-(6-oxo-6H-pyridazin-1-yl)-propionic acid (2.45 g, 86%) as a light pink solid; ES+-HRMS m/e calcd for C12H16N2O3 [M+H+] 237.1234, found 237.1233.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. customThe residue was partitioned between water (100 mL) which
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d2bed4eec58a40439f699d01e13acb2a
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258134B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes