Methanol → HCID 23373472, compound

HRID 1461100Notes

Reaction equation

HRID 1461100 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-yl-carbonyl)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-60822d5d7e89409b82a37f7031099fb0
Source dataset
uspto-grants-1991_12
Patent number
US05073566

Reaction notes

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