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Triphenylphosphine → 2-[(4-{2-[(5-Bromopyridin-2-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914318
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HRID 914318 반응식
[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][OH:18])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Br:20][C:21]1[CH:22]=[CH:23][C:24](O)=[N:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OC(C)C)=O)(C(OC(C)C)=O)=[N-]>O1CCCC1>[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:24]2[CH:23]=[CH:22][C:21]([Br:20])=[CH:26][N:25]=2)[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:4])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 22145704Diisopropyl diazodicarboxylateHCID 597593522-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl esterHCID 178515818HCID 178515818, 화합물

생성물 1

HCID 597591722-[(4-{2-[(5-Bromopyridin-2-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester수율 57.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (2.12 g) synthesized in Example 4 and 5-bromopyridin-2-ol (1.22 g) were dissolved in tetrahydrofuran (20 mL), triphenylphosphine (2.02 g) and diisopropyl diazodicarboxylate (40% toluene solution, 4.14 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and hexane (about 10 mL) was added. The precipitated crystals were removed by filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (1.84 g) as a pale-yellow oil.

후처리

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and hexane (about 10 mL)
  3. additionwas added
  4. customThe precipitated crystals were removed by filtration
  5. customthe solvent of the filtrate was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-3dc2015238ec4ad682d305188b36677e
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08026370B2

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