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

HRID 643506
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HRID 643506 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-62874e7a10fd4e0c8e2377faaf3a635e
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07700605B2

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