Methanol → HCID 23373472, compound

HRID 1899421Notes

Reaction equation

HRID 1899421 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[N:6]1[CH:10]=[C:9]([NH:11][C:12]([CH:14]2[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[N:8]=[CH:7]1)C.[OH-:34].[K+].CO.O>C(OCC)(=O)C>[CH2:27]([CH:5]([N:6]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2([OH:34])[C:26]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:13])[N:8]=[CH:7]1)[C:4]([OH:3])=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 54350304HCID 54350304, compound

Product 1

HCID 23373472HCID 23373472, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

When 2.1 g of α-hexyl-4-[(9H-fluoren-9-ylcarbonyl)amino]-1H-imidazole-1-acetic acid ethyl ester was heated with 3.0 g of potassium hydroxide, 30 ml of methanol, and 15 ml of water at reflux for one hour, upon adjustment of pH to 3.8, a thick oil formed. The oil was dissolved in ethyl acetate and separated from the aqueous layer. The organic layer was dried and concentrated in vacuo. The oil was taken up in ethanol and saturated with hydrogen chloride gas. The resulting product was purified by high pressure liquid chromatography to provide 0.370 g of the titled product, m.p. 128° C.

Workup

  1. temperatureat reflux for one hour, upon adjustment
  2. customa thick oil formed
  3. customseparated from the aqueous layer
  4. customThe organic layer was dried
  5. concentrationconcentrated in vacuo
  6. customThe resulting product was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-c7de5fb31e5b40cd8e8d21903a1e573a
Source dataset
uspto-grants-1996_11
Patent number
US05571925

Reaction notes

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