Hydrochloric Acid → HCID 20081441, compound

HRID 1609446Notes

Reaction equation

HRID 1609446 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([NH:24][S:25]([CH:28]([CH:32]([CH3:34])[CH3:33])[C:29]([NH2:31])=O)(=[O:27])=[O:26])[N:17]=1.N1C=CC=CC=1.Cl>O1CCOCC1.O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[N:19]=[C:18]([NH:24][S:25]([CH:28]([CH:32]([CH3:34])[CH3:33])[C:29]#[N:31])(=[O:27])=[O:26])[N:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 20081446HCID 20081446, compound

Product 1

HCID 20081441HCID 20081441, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Trifluoroacetic anhydride (0.73 g) was added to a stirred, ice-cooled solution of the product of Example 20 in dioxan (10 ml) containing pyridine (0.5 g). After stirring for 11/2 hours at room temperature, the mixture was added to water (100 ml) and acidified with hydrochloric acid. The liberated product was extracted into ether, and the ether solution was washed with water (twice), dried over magnesium sulfate and run down. The residual oil was flash chromatographed on silica gel, eluting with 30% ethyl acetate in dichloromethane, to give, after trituration with petroleum ether (bp 40°-60° C.), 0.3 g of the desired product, mp 91°-93° C., as a white solid.

Workup

  1. extractionThe liberated product was extracted into ether
  2. washthe ether solution was washed with water (twice),
  3. dry with materialdried over magnesium sulfate
  4. customchromatographed on silica gel
  5. washeluting with 30% ethyl acetate in dichloromethane
  6. customto give

Sources & evidence

ORD record
ord-63f8f10cab53420daff0e72f5410130d
Source dataset
uspto-grants-1995_03
Patent number
US05401710

Reaction notes

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