Triphenylphosphine → 3-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyrimidin-4-ylmethoxy)phenyl]-propionic acid ethyl ester

HRID 62936노트

반응식

HRID 62936 반응식
[CH:1]([S:4][C:5]1[N:10]=[C:9]([CH2:11][OH:12])[CH:8]=[CH:7][N:6]=1)([CH3:3])[CH3:2].[CH2:13]([O:15][C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([F:25])[C:22](O)=[C:21]([F:27])[CH:20]=1)[CH3:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH2:13]([O:15][C:16](=[O:28])[CH2:17][CH2:18][C:19]1[CH:24]=[C:23]([F:25])[C:22]([O:12][CH2:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH:1]([CH3:3])[CH3:2])[N:10]=2)=[C:21]([F:27])[CH:20]=1)[CH3:14]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 23136305Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoateHCID 90118246(2-Isopropylsulfanyl-pyrimidin-4-yl)-methanol

생성물 1

HCID 901184523-[3,5-Difluoro-4-(2-isopropylsulfanyl-pyrimidin-4-ylmethoxy)phenyl]-propionic acid ethyl ester수율 82.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2-Isopropylsulfanyl-pyrimidin-4-yl)-methanol (0.08 g, 0.43 mmol) obtained in Step C of Preparation Example 24, 3-(3,5-difluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (0.1 g, 0.43 mmol) obtained in Step D of Preparation Example 2 and triphenyl phosphine (0.114 g, 0.43 mmol) were dissolved in anhydrous THF (3 mL), and the mixture was stirred at room temperature for 10 minutes. Diisopropyl azodicarboxylate (0.085 mL, 0.43 mmol) was added slowly thereto. The mixture was stirred at room temperature for 18 hours, concentrated under reduced pressure, and separated by column chromatography (eluent: 100% DCM) to obtain the title compound (0.14 g, 81%).

후처리

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. customseparated by column chromatography (eluent: 100% DCM)

출처 및 근거

ORD 기록
ord-51b33dac48314a61aef22e2df7ae2823
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447044B2

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