Acetic Acid → HCID 19010330, compound

HRID 1741604Notes

Reaction equation

HRID 1741604 reaction equation
C([O:4][CH:5]([C:7]1[CH:8]=[N:9][C:10]([C:17]2[NH:18][C:19](=[O:26])[C:20]([CH:23]([CH3:25])[CH3:24])([CH3:22])[N:21]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[CH3:6])(=O)C.C[O-].[Na+].C(O)(=O)C>CO>[OH:4][CH:5]([C:7]1[CH:8]=[N:9][C:10]([C:17]2[NH:18][C:19](=[O:26])[C:20]([CH:23]([CH3:25])[CH3:24])([CH3:22])[N:21]=2)=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 19010312HCID 19010312, compound

Product 1

HCID 19010330HCID 19010330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 16 g of methyl 5-(1-acetoxyethyl)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate and 0.5 g sodium methoxide in 150 mL methanol is stirred at room temperature under nitrogen for 5 days. The reaction is acidified to pH 5 with acetic acid and concentrated in vacuo. The residue is partitioned between methylene chloride and water, the aqueous layer is further extracted with methylene chloride, and the combined organic phases are dried over sodium sulfate and concentrated in vacuo to an orange oil. Column chromatography of this oil using ether-hexane as eluent affords the desired product as a white foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is partitioned between methylene chloride and water
  3. extractionthe aqueous layer is further extracted with methylene chloride
  4. dry with materialthe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated in vacuo to an orange oil

Sources & evidence

ORD record
ord-5e1eee56303047d68b88514850c77836
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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