Water → HCID 20638859, compound

HRID 1276551Notes

Reaction equation

HRID 1276551 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@:9]2([OH:24])[CH2:17][C@H:16]3[C@@:12]([CH3:23])([C@@H:13]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:14][CH2:15]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C[S-].[Na+].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@:9]2([OH:24])[CH2:17][C@H:16]3[C@@:12]([CH3:23])([C@@H:13]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:14][CH2:15]3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@:9]2([OH:24])[CH2:17][C@H:16]3[C@@:12]([CH3:23])([C@@H:13]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:14][CH2:15]3)[CH2:11][CH2:10]2)=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 57025299HCID 57025299, compound

Product 2

HCID 20638859HCID 20638859, compoundHCID 57025299HCID 57025299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of 5.45 g (16.4 mmol) of compound A, presented according to Example 1a, in 70 ml of anhydrous dimethylformamide is mixed under an atmosphere of dry argon with 5.65 g of sodium methanethiolate, and it is heated for about 5 hours to 170° C. After cooling, it is poured into water, extracted several times with ethyl acetate, the combined organic extracts are washed with saturated sodium chloride solution and dried on sodium sulfate. The residue that is obtained after filtration and removal of the solvent is combined with the crude product that is obtained in Example 1b and purified by chromatography on about 800 ml of fine silica gel with a gradient system that consists of n-hexane and ethyl acetate. 8.00 g (26.6 mmol, 65% relative to products A and B that are obtained in Example 1a) of title compound A and 1.85 g (5.81 mmol, 14% relative to products A and B that are obtained in Example 1a) of title compound B are isolated in each case as a colorless foam.

Workup

  1. temperatureis heated for about 5 hours to 170° C
  2. temperatureAfter cooling
  3. extractionextracted several times with ethyl acetate
  4. washthe combined organic extracts are washed with saturated sodium chloride solution
  5. customdried on sodium sulfate
  6. customThe residue that is obtained
  7. filtrationafter filtration and removal of the solvent
  8. customis obtained in Example 1b
  9. custompurified by chromatography on about 800 ml of fine silica gel with a gradient system that

Sources & evidence

ORD record
ord-0c9e4ef643644757b2b91dc045f4fb4e
Source dataset
uspto-grants-2000_12
Patent number
US06166075

Reaction notes

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