Triphenylphosphine → HCID 59759128, compound

HRID 914518Notes

Reaction equation

HRID 914518 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].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N+:39]([C:42]1[CH:47]=[CH:46][C:45]([C:48]2[CH:53]=[CH:52][C:51](O)=[CH:50][CH:49]=2)=[CH:44][CH:43]=1)([O-:41])=[O:40].N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6](=[O:19])[C:7]([CH3:9])([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:51]2[CH:50]=[CH:49][C:48]([C:45]3[CH:46]=[CH:47][C:42]([N+:39]([O-:41])=[O:40])=[CH:43][CH:44]=3)=[CH:53][CH:52]=2)[N:15]=1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 1380784-Hydroxy-4'-nitrobiphenylHCID 597593522-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 59759128HCID 59759128, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (2.7 g) synthesized in Example 4 in tetrahydrofuran (15 ml) were added triphenylphosphine (2.5 g) and 4-(4-nitrophenyl)phenol (12.1 g), and the mixture was stirred under ice-cooling for 5 min. To the solution was added diisopropyl azodicarboxylate (40% toluene solution, 4.7 ml), and the mixture was stirred at room temperature overnight. To the solution were further added triphenylphosphine (1.2 g) and diisopropyl azodicarboxylate (40% toluene solution, 2.4 ml), and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was concentrated, extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (3.3 g) as a pale-brown solid.

Workup

  1. temperaturecooling for 5 min
  2. stirringthe mixture was stirred at room temperature overnight
  3. stirringthe mixture was stirred at room temperature for 3.5 hr
  4. concentrationThe reaction mixture was concentrated
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with aqueous sodium hydroxide solution and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fe3baeb902504bf7b35b3c153a87637c
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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