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

HRID 846451Notes

Reaction equation

HRID 846451 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.[CH:33]([C:35]1[CH:36]=[C:37]([CH:41]([S:49][CH2:50][CH2:51][C:52](=[O:56])[N:53]([CH3:55])[CH3:54])[S:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:38]=[CH:39][CH:40]=1)=O.C([O-])(=O)C.[NH4+]>C1COCC1.CCCCCC>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9]([CH:13]=[CH:33][C:35]3[CH:36]=[C:37]([CH:41]([S:49][CH2:50][CH2:51][C:52](=[O:56])[N:53]([CH3:55])[CH3:54])[S:42][CH2:43][CH2:44][C:45]([O:47][CH3:48])=[O:46])[CH:38]=[CH:39][CH:40]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 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 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a suspension of 7-chloroquinolin-2-ylmethyltriphenylphosphonium 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 mM). 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-f1fa7e92634145bfb5cf35956353523f
Source dataset
uspto-grants-1992_08
Patent number
US05136034

Reaction notes

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