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

HRID 62936ノート

反応式

HRID 62936 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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%).

後処理

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

出典と根拠

ORDレコード
ord-51b33dac48314a61aef22e2df7ae2823
出典データセット
uspto-grants-2016_09
特許番号
US09447044B2

反応ノート

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