Hexane → (+)-Methyl 5-(3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 846454Notes

Reaction equation

HRID 846454 reaction equation
[Br-].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH2:13][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:10]2)=[CH:5][CH:4]=1.CCCCCC.[CH:39]([C:41]1[CH:42]=[C:43]([CH:47]([S:55][CH2:56][CH2:57][C:58](=[O:62])[N:59]([CH3:61])[CH3:60])[S:48][CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])[CH:44]=[CH:45][CH:46]=1)=O.C([O-])(=O)C.[NH4+]>C1COCC1>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[CH:39][C:41]3[CH:42]=[C:43]([CH:47]([S:55][CH2:56][CH2:57][C:58](=[O:62])[N:59]([CH3:61])[CH3:60])[S:48][CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52])[CH:44]=[CH:45][CH:46]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 517165Ammonium AcetateHCID 10391903((7-Chloroquinolin-2-yl)methyl)triphenylphosphonium bromideHCID 19930537(+)-Methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Product 1

HCID 86743269(+)-Methyl 5-(3-(2-(7-chloroquinolin-2-yl)ethenyl)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a suspension of 7-chloroquinolin-2-ylmethyltriphenylphosphonium bromide (Example 4, Step 2) (809 mg, 1.56 mmol.) in THF (15 mL) at -78° C., was added a solution of n-Buli (1.6 M) in hexane (0.89 mL, 1.43 mmol.). The mixture was stirred for 0.5 hrs at -78° C. Then, (+)-methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate (step 3) (480 mg, 1.3 mmol.) in THF (4 mL) was slowly added. The mixture was stirred for 0.5 hr at -78° C. and then warmed up to room temperature and stirred for an additional 2 hrs. A solution of 25% ammonium acetate was added, the mixture was extracted with ethyl acetate, and the extracts were washed with brine (3×), dried over sodium sulfate, filtered and evaporated to dryness. Purification by flash chromatography afforded the title compound.

Workup

  1. stirringThe mixture was stirred for 0.5 hr at -78° C.
  2. temperaturewarmed up to room temperature
  3. stirringstirred for an additional 2 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe extracts were washed with brine (3×)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customPurification by flash chromatography

Sources & evidence

ORD record
ord-04ad8079b55441f5b47b7f29c952d310
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Reaction notes

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