Tributylphosphine → 3-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester

HRID 860701노트

반응식

HRID 860701 반응식
[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[O:23][C:24]([CH:30](O)[CH3:31])=[C:25]([CH:27]([CH3:29])[CH3:28])[N:26]=2)=[CH:18][CH:17]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:14])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:30]([C:24]2[O:23][C:22]([C:19]3[CH:20]=[CH:21][C:16]([Br:15])=[CH:17][CH:18]=3)=[N:26][C:25]=2[CH:27]([CH3:28])[CH3:29])[CH3:31])=[CH:8][C:7]=1[CH3:13]

참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 13551833Methyl 3-(4-Hydroxy-2-methylphenyl)propanoateHCID 587656641-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol

생성물 1

HCID 101521383-(4-{1-[2-(4-Bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethoxy}-2-methyl-phenyl)-propionic acid methyl ester수율 83.1%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (6.30 g, 32.1 mmol) and 1-[2-(4-bromo-phenyl)-4-isopropyl-oxazol-5-yl]-ethanol (9.05 g, 29.2 mmol) in toluene (300 mL) is degassed and filled with nitrogen for 3 times. Tributylphosphine (7.70 g, 38.1 mmol) is added to the reaction mixture under nitrogen at 0° C., followed by addition of of 1,1′-(azodicarbonyl)-dipiperidine (8.84 g, 35.0 mmol). The reaction mixture is allowed to warm to room temperature and stirred overnight, the mixture is loaded directly on silica gel column chromatography with 10–15% EtOAc/Hexanes to afford the title compound (11.8 g, 79%).

후처리

  1. additionfilled with nitrogen for 3 times

출처 및 근거

ORD 기록
ord-3be89de06aa04407b92b958c9d1c264f
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153878B2

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