Pyridine → HCID 178458846, compound

HRID 477405Notes

Reaction equation

HRID 477405 reaction equation
N1C=CC=CC=1.[CH3:7][S:8](Cl)(=[O:10])=[O:9].[C:12]([C:16]1[C:17](=[O:33])[CH2:18][CH:19]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[C:25]([NH2:31])[C:24]=2[CH3:32])[CH2:20][C:21]=1[OH:22])(=[O:15])[CH2:13][CH3:14]>C(Cl)Cl>[C:12]([C:16]1[C:17](=[O:33])[CH2:18][CH:19]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[C:25]([NH:31][S:8]([CH3:7])(=[O:10])=[O:9])[C:24]=2[CH3:32])[CH2:20][C:21]=1[OH:22])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178458842HCID 178458842, compound

Product 1

HCID 178458846HCID 178458846, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.53 ml, 6.6 mmol) followed by methane sulfonyl chloride (0.52 ml, 6.6 mmol) was added to a stirred solution of 2-propionyl-3-hydroxy-5-(3-amino-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (1.0 g, 3.3 mmol)in methylene chloride (10 ml). Stirring was continued at 20° for 8 hr. The organic layer was washed with water, dilute hydrochloric acid and further water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude product. The crude material was purified by column chromatography on silica gel (elution with an increasing gradient of methanol in methylene chloride) to give 2-propionyl-3-hydroxy- 5-(3-methylsulphonamido-2,4,6-trimethylphenyl)cyclohex-2-en-1-one as a yellow waxy solid (0.6 g, 50%). The compound was characterized by proton magnetic resonance spectroscopy (CDCl3 ; δ in ppm): 1.17 (3H,t); 2.35 6H, s); 2.46 (3H,s); 3.0 (3H,s); 2.4-4.1 (7H,m); 6.78 (1H,s); 6.89 (1H,s); 18.15 (1H,brs).

Workup

  1. washThe organic layer was washed with water, dilute hydrochloric acid and further water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto yield the crude product
  5. customThe crude material was purified by column chromatography on silica gel (
  6. washelution with an increasing gradient of methanol in methylene chloride)

Sources & evidence

ORD record
ord-9a0ab4bc772240ae99bc31a4f3ab6a40
Source dataset
uspto-grants-1989_12
Patent number
US04888043

Reaction notes

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