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

HRID 232431

Reaction equation

HRID 232431 reaction equation
[Br-].[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([C:13]3C=CC=CC=3[P+](C)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:10]2)=[CH:5][CH:4]=1.[Li]CCCC.CCCCCC.[CH:44]([C:46]1[CH:47]=[C:48]([CH:52]([S:60][CH2:61][CH2:62][C:63](=[O:67])[N:64]([CH3:66])[CH3:65])[S:53][CH2:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])[CH:49]=[CH:50][CH:51]=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:44][C:46]3[CH:47]=[C:48]([CH:52]([S:60][CH2:61][CH2:62][C:63](=[O:67])[N:64]([CH3:66])[CH3:65])[S:53][CH2:54][CH2:55][C:56]([O:58][CH3:59])=[O:57])[CH:49]=[CH:50][CH:51]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 8058HexaneHCID 517165Ammonium AcetateHCID 19930537(+)-Methyl 5-(3-formylphenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoateHCID 867432707-Chloroquinolin-2-yl-methyltriphenylphosphonium bromideHCID 178418339Butyllithium

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-yl-methyltriphenylphosphonium bromide (809 mg, 1.56 mmol.) (Example 4, Step 2) in THF (15 mL) at -78° C., was added a solution of n-BuLi (1.6M) 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 7) (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-47550c39ae6645698acb8e352fa8740f
Source dataset
uspto-grants-1989_07
Patent number
US04851409

Linked notes

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