Hydrochloric Acid → HCID 21480504, compound

HRID 1490043Notes

Reaction equation

HRID 1490043 reaction equation
O1CC[O:3][CH:2]1[C:6]1[CH:10]=[CH:9][S:8][C:7]=1[S:11]([NH:14][CH2:15][CH2:16][OH:17])(=[O:13])=[O:12].[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl.[CH:28]([O:30][CH2:31][CH3:32])=[CH2:29].C(=O)(O)[O-].[Na+]>CN(C=O)C.C1COCC1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][N:14]([CH2:15][CH2:16][O:17][CH:28]([O:30][CH2:31][CH3:32])[CH3:29])[S:11]([C:7]1[S:8][CH:9]=[CH:10][C:6]=1[CH:2]=[O:3])(=[O:12])=[O:13])[CH3:26]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 8023Ethyl vinyl etherHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 54061678HCID 54061678, compound

Product 1

HCID 21480504HCID 21480504, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product from Step A (11.55 g, 41.4 mmol) in anhydrous DMF (200 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 1.74 g, 43.5 mmol). After 30 min ethyl bromoacetate (5.51 mL, 6.33 g, 49.7 mmol) was added; this solution was stirred for about 7 min and 2N HCl (100 mL) added. The resulting mixture was stirred at ambient temperature for 2 h, poured into ice-water (300 mL) and extracted with ethyl acetate (2×300 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness to give a viscous oil which was dissolved in THF (50 mL), p-TsOH (0.1 g) was added and the solution cooled on an ice bath followed by the addition of ethyl vinyl ether (7.86 mL, 82.2 mmol). After stirring for 1 h a saturated solution of sodium bicarbonate (100 mL) was added and the mixture was extracted with ethyl acetate (2×200 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to dryness. Column chromatography (silica, 30% ethyl acetate in hexane) gave the desired product as a viscous oil (10.21 g, 63%).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 2 h
  2. extractionextracted with ethyl acetate (2×300 mL)
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a viscous oil which
  7. temperaturethe solution cooled on an ice bath
  8. additionwas added
  9. extractionthe mixture was extracted with ethyl acetate (2×200 mL)
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-49c41f989f164edc83569f0e182dbe49
Source dataset
uspto-grants-1997_10
Patent number
US05681834

Reaction notes

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