Methanesulfonyl chloride → HCID 18979131, compound

HRID 2393181Notes

Reaction equation

HRID 2393181 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]COC)=[O:19].[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>N1C=CC=CC=1.Cl>[S:24]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])([CH3:27])(=[O:26])=[O:25]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18979130HCID 18979130, compound

Product 1

HCID 18979131HCID 18979131, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

In pyridine (3 ml) was dissolved methoxymethyl 7-(1-amino-2-naphthyl)heptanoate (0.3 g) followed by addition of mesyl chloride (0.218 g), and the mixture was stirred at 50° C. for 2 hours. This reaction mixture was poured in 0.5N HCl and extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated to dryness. The residue was treated with 1N HCl (3 ml) and tetrahydrofuran (6 ml) at the reflux temperature for 1.5 hours and, after cooling, extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated to dryness, and the residue was recrystallized from hexane-diisopropyl ether to provide 7-(1-mesylamino-2-naphthyl)heptanoic acid (0.281 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated to dryness
  5. additionThe residue was treated with 1N HCl (3 ml) and tetrahydrofuran (6 ml) at the reflux temperature for 1.5 hours
  6. temperatureafter cooling
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. customdried
  10. concentrationconcentrated to dryness
  11. customthe residue was recrystallized from hexane-diisopropyl ether

Sources & evidence

ORD record
ord-f400a2d39b82438bad1c1cea4f6c967a
Source dataset
uspto-grants-1998_09
Patent number
US05804601

Reaction notes

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