Methanesulfonyl chloride → HCID 20158410, compound

HRID 986326Notes

Reaction equation

HRID 986326 reaction equation
[Cl:1][C:2]1[C:3](=[O:36])[CH:4]([CH:25]([OH:35])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:5]([O:20][Si:21]([CH3:24])([CH3:23])[CH3:22])([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH:6]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].N12CCCN=C1CCCCC2.S([O-])(O)(=O)=O.[K+]>N1C=CC=CC=1>[Cl:1][C:2]1[C:3](=[O:36])[CH:4]([CH:25]([O:35][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:5]([O:20][Si:21]([CH3:22])([CH3:24])[CH3:23])([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH:6]=1.[Cl:1][C:2]1[C:3](=[O:36])[C:4](=[CH:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])[C:5]([O:20][Si:21]([CH3:22])([CH3:24])[CH3:23])([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[C:12]([O:18][CH3:19])[CH:11]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 516920Potassium bisulfateHCID 20158416HCID 20158416, compound

Product 2

HCID 20158410HCID 20158410, compoundYield 28%HCID 54021683HCID 54021683, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

46 mg of 2-chloro-4-trimethylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(1-hydroxy-6-methoxycarbonylhexyl)-2-cyclopentenone was dissolved in 1 ml of pyridine, and 100 microliters of methanesulfonyl chloride was added. The mixture was stirred for 2.5 hours. 150 microliters of 1,8-diazabicyclo[5.4.0]undec-7-ene was added, and the mixture was stirred for 6 hours. A saturated aqueous solution of potassium hydrogen sulfate was added, and the mixture was extracted with ethyl acetate. The organic layers were combined, washed successively with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride. After filtration and concentration, the residue was chromatographed on a silica gel column to give 15 mg (yield 28%) of 2-chloro-4-tri-methylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(1-methanesulfonyloxy-6-methoxycarbonylhexyl)-2-cyclopentenone and 7.7 mg (yield 17%) of 2-chloro-4-trimethylsilyloxy-4-[3-(3,4-dimethoxyphenyl)propyl]-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed successively with a saturated aqueous solution of sodium hydrogen carbonate
  4. filtrationAfter filtration and concentration
  5. customthe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-f313bb2d6d1a4cfcad4f84964ed9c720
Source dataset
uspto-grants-1987_12
Patent number
US04711895

Reaction notes

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