Hydrochloric Acid → HCID 21401649, compound

HRID 1730124Notes

Reaction equation

HRID 1730124 reaction equation
[H-].[Na+].[C:3]([O:6][CH:7]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH2:8][CH2:9][CH2:10][NH:11][S:12]([CH3:15])(=[O:14])=[O:13])(=[O:5])[CH3:4].[H][H].Br[CH2:28][C:29]#[C:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35].Cl>O.CN(C)C=O.C1C=CC=CC=1>[C:3]([O:6][CH:7]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[CH2:8][CH2:9][CH2:10][N:11]([CH2:28][C:29]#[C:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[S:12]([CH3:15])(=[O:14])=[O:13])(=[O:5])[CH3:4]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 11287432Methyl 7-bromohept-5-ynoateHCID 21401585HCID 21401585, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21401649HCID 21401649, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred suspension of sodium hydride (57%) (.91 g., 0.022 mole) in a solvent mixture of benzene (50 ml.) and dimethylformamide (50 ml.) is treated, over 30 minutes, with N-[4-acetoxy-5-(4-fluorophenoxy)pentyl] -methanesulfonamide (6.5 g., 0.02 mole). This mixture is heated at 60° C. until evolution of hydrogen ceases, then cooled to room temperature. At this temperature is added methyl 7-bromo-5-heptynoate (4.3 g., 0.02 mole) and the reaction is heated at 90° C. for 3 hours. The reaction is poured into water (200 ml.), neutralized with hydrochloric acid and extracted with ethyl acetate (2 × 100 ml.). The ethyl acetate layer is washed with brine, dried over sodium sulfate, then concentrated in vacuo. The product is purified by chromatography over silica gel using 5% methanol in chloroform to elute. Evaporation of the appropriate fractions affords the subject compound as a yellow oil.

Workup

  1. temperaturethe reaction is heated at 90° C. for 3 hours
  2. extractionextracted with ethyl acetate (2 × 100 ml.)
  3. washThe ethyl acetate layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe product is purified by chromatography over silica gel using 5% methanol in chloroform
  7. washto elute
  8. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-783cdaac324b48ea8fe4c5809d3e8c68
Source dataset
uspto-grants-1976_11
Patent number
US03991106

Reaction notes

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