Imidazole → tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 16329

反応式

HRID 16329 の反応式
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([OH:34])[CH3:33])([CH3:27])([CH3:26])[CH3:25].N1C=CN=C1>O.C(OCC)(=O)C>[C:24]([O:28][C:29](=[O:44])[NH:30][C@H:31]([C:35]1[CH:40]=[C:39]([F:41])[C:38]([F:42])=[C:37]([F:43])[CH:36]=1)[C@H:32]([O:34][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:33])([CH3:25])([CH3:26])[CH3:27]

参加物

7

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 94078tert-ButyldiphenylchlorosilaneHCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

生成物 1

HCID 68718850tert-butyl [(1R,2R)-2-(tert-butyldiphenylsilanyloxy)-1-(3,4,5-trifluorophenyl)propyl]carbamate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In nitrogen atmosphere, tert-butyldiphenylsilyl chloride (2.0 mL) was added dividedly four times to a DMF solution (3 mL) of [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]-carbamic acid tert-butyl ester (610 mg) and imidazole (817 mg). This reaction solution was stirred at room temperature for 3 hr. To the reaction solution, ethyl acetate and water were added. The organic layer was separated, washed with 1 N hydrochloric acid, water, a saturated sodium hydrogencarbonate aqueous solution, and saturated saline in this order. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1) to give 684 mg of the title compound. The physical property values of this compound were as follows:

後処理

  1. customThe organic layer was separated
  2. washwashed with 1 N hydrochloric acid, water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: hexane:diethylether=49:1 to 19:1)

出典と根拠

ORDレコード
ord-cbe249a5d1264e269f037a95cd7c9cbc
出典データセット
uspto-grants-2010_06
特許番号
US07737141B2

関連ノート

読み込み中…