Triphenylphosphine → HCID 59759175, compound

HRID 914330Notes

Reaction equation

HRID 914330 reaction equation
[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:26]=[CH:25][C:24](O)=[C:23]([F:28])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+](C(OCC)=O)(C(OCC)=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:25]=[CH:26][C:21]([Br:20])=[CH:22][C:23]=2[F:28])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 27249814-Bromo-2-fluorophenolHCID 14357405DiethyldiazodicarboxylateHCID 597593522-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 59759175HCID 59759175, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (3.0 g) synthesized in Example 4 and 4-bromo-2-fluorophenol (1.91 g) were dissolved in tetrahydrofuran (20 mL), triphenylphosphine (2.62 g) and diethyl diazodicarboxylate (1.74 g) were added under ice-cooling, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=6:1) to give the title compound (3.2 g) as a colorless oil.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-8e5554f3dfc14e8ba98a110e40e19f84
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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