Dimethylformamide → HCID 178450085, compound

HRID 1368534Notes

Reaction equation

HRID 1368534 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([C:24]1[N:25]=[CH:26][N:27](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:28]=1)([OH:23])[CH:20]([CH3:22])[CH3:21])[CH:13]=[CH:12]2.[C:48]([O:54][CH2:55]I)(=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50]>C(OCC)(=O)C.O>[CH3:50][C:49]([CH3:52])([CH3:51])[C:48]([O:54][CH2:55][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:23])([C:24]3[N:25]=[CH:26][NH:27][CH:28]=3)[CH:20]([CH3:22])[CH3:21])[CH:15]=2)[CH:10]=1)=[O:53]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 104401Iodomethyl pivalateHCID 220183856-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthol

Product 1

HCID 178450085HCID 178450085, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% oil dispersion, 0.120 g) was added to DMF (15 ml), and to the mixture was slowly added 1-(6-hydroxynaphthalen-2-yl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (1.397 g) under ice cooling, and the mixture was stirred for 30 min under ice cooling. To the mixture was added iodomethyl pivalate (0.83 g), and the mixture was stirred at room temperature for 6 h. To the mixture were added water and ethyl acetate, and the organic layer was washed with water and saturated solution of sodium chloride. The extract was dried and concentrated. The obtained residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=5:1→3:1). Recrystallization from hexane-ethyl acetate to give the titled compound (0.433 g) as a colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 h
  2. washthe organic layer was washed with water and saturated solution of sodium chloride
  3. customThe extract was dried
  4. concentrationconcentrated
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=5:1→3:1)
  6. customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-5f5c8c2ed56341c4b3900a3ea726ccbd
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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