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Sodium Carbonate → [2-(3'-Hydroxy-biphenyl-4-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 643506
ノート
印刷プレビュー

反応式

HRID 643506 の反応式
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[OH:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O.O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:18])[CH:24]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 75806TricyclohexylphosphineHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 14221818[2-(4-Bromo-phenyl)ethyl]-carbamic acid tert-butyl ester

生成物 1

HCID 68578938[2-(3'-Hydroxy-biphenyl-4-yl)-ethyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of [2-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (500 mg), 3-hydroxybenzeneboronic acid (296 mg), sodium carbonate (265 mg), palladium (II) acetate (7 mg) and tricyclohexylphosphine (10 mg) in water (3 ml) and dioxane (12 ml) is kept at 90° C. under micro wave conditions for 180 min. The mixture is cooled down to rt and is filtered through an EXTUBE extraction column (Varian) with EtOAc (200 ml). The filtrate is evaporated and the resulting crude product is purified on silica (150 g) with cyclohexane/EtOAc 5/1 to afford pure [2-(3′-hydroxy-biphenyl-4-yl)-ethyl]-carbamic acid tert-butyl ester.

後処理

  1. filtrationis filtered through an EXTUBE extraction column (Varian) with EtOAc (200 ml)
  2. customThe filtrate is evaporated
  3. customthe resulting crude product is purified on silica (150 g) with cyclohexane/EtOAc 5/1

出典と根拠

ORDレコード
ord-62874e7a10fd4e0c8e2377faaf3a635e
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700605B2

反応ノート

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