Triphenylphosphine → HCID 69432329, compound

HRID 1348958Notes

Reaction equation

HRID 1348958 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:32][O:33][C:34]([C:36]1[NH:37][C:38](=[O:50])[NH:39][C:40]=1[CH2:41][S:42][C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1)=[O:35].[CH3:51][C:52]1[CH:61]=[C:60]([CH2:62]O)[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[N:53]=1>C1COCC1.CN(C=O)C>[CH3:32][O:33][C:34]([C:36]1[NH:37][C:38](=[O:50])[NH:39][C:40]=1[CH2:41][S:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH2:62][C:60]2[C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[N:53]=[C:52]([CH3:51])[CH:61]=2)=[CH:45][CH:44]=1)=[O:35]

Participants

7

Reactant 4

HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylateHCID 10149033(2-Methylquinolin-4-yl)methanolHCID 711950995-(4-hydroxy-phenylsulfanyl methyl)-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester

Product 1

HCID 69432329HCID 69432329, compoundYield 8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of DEAD (81 mg, 0.46 mmol) in 3 mL of THF at 0° C. was added PPh3 (120 mg, 0.46 mmol). After dissolution of PPh3, 4d (100 mg, 0.31 mmol) was added and the solution was stirred for 15 min. (2-methyl-4-quinolinyl)methanol was then added as a solid. After stirring for 2 h, 3 mL of DMF was added to aid dissolution. The mixture was stirred at room temperature overnight before it was quenched with water. The solution was extracted with CH2Cl2 and the organic layer was dried over MgSO4. After filtration and concentration, the residue was purified by flash column chromatography to provide 5-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylsulfanylmethyl]-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 4e (11 mg, 8%). MS (ESI+) (M+1)=436.

Workup

  1. additionwas added
  2. additionwas then added as a solid
  3. stirringThe mixture was stirred at room temperature overnight before it
  4. customwas quenched with water
  5. extractionThe solution was extracted with CH2Cl2
  6. dry with materialthe organic layer was dried over MgSO4
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-f3ab5768211b4e6a88490fda4322a720
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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