Water → HCID 18349795, compound

HRID 2268248Notes

Reaction equation

HRID 2268248 reaction equation
[CH3:1][C:2]1(C)[CH2:6][O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([NH:16][CH2:17][CH:18]([OH:25])[CH2:19][N:20]3[CH:24]=[CH:23][N:22]=[CH:21]3)([CH3:15])[CH3:14])=[CH:9][CH:8]=2)=N1.S(=O)(=O)(O)[OH:28].O>C(O)CC>[OH:25][CH:18]([CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[CH2:17][NH:16][C:13]([C:10]1[CH:11]=[CH:12][C:7]([C:4]([O:5][CH2:6][CH2:2][CH3:1])=[O:28])=[CH:8][CH:9]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric Acid2×HCID 18349566HCID 18349566, compound

Product 1

HCID 18349795HCID 18349795, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent3×

Procedure

A mixture of 1-{1-[4-(4,4-dimethyl-2-oxazolin-2-yl)phenyl]-1-methylethylamino}-3-(imidazol-1-yl)propan2-ol (100 mg) and a solution of sulphuric acid in propan-1-ol (5 ml) [prepared by adding concentrated sulphuric acid (4 ml) and then water (5 ml) to propan-1-ol (50 ml) and making up to 100 ml with propan-1-ol] was heated on a steam bath for 18 hours. The mixture was evaporated under reduced pressure. The residue was basified with aqueous sodium hydroxide solution and then extracted with dichloromethane to give a residue which was purified by flash column chromatography on silica using ethyl acetate/triethylamine (9:1) with increasing amounts of ethanol to give propyl 4-{1-[2-hydroxy-3-(imidazol-1-yl)propylamino]-1-methylethyl}benzoate as an oil.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. customThe mixture was evaporated under reduced pressure
  3. extractionextracted with dichloromethane
  4. customto give a residue which
  5. customwas purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-c99ad87fe4424fb4b053999a877ec236
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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