Dimethylformamide → HCID 178450085、化合物

HRID 1368534ノート

反応式

HRID 1368534 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 178450085HCID 178450085、化合物収率 41%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5f5c8c2ed56341c4b3900a3ea726ccbd
出典データセット
uspto-grants-2003_06
特許番号
US06573289B1

反応ノート

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