Trifluoroacetic anhydride → HCID 54384384, compound

HRID 2393332Notes

Reaction equation

HRID 2393332 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:14]([N:17]([CH2:29][CH2:30][C:31]([OH:33])=O)[C:18]([NH:20][C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])=[S:19])[CH:15]=[CH2:16].C([O-])(O)=O.[Na+]>>[CH2:14]([N:17]1[CH2:29][CH2:30][C:31](=[O:33])[N:20]([C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:28])[C:18]1=[S:19])[CH:15]=[CH2:16]

Participants

4

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 516892Sodium BicarbonateHCID 18975633HCID 18975633, compound

Product 1

HCID 54384384HCID 54384384, compoundYield 49.7%

Procedure

To a cooled solution of trifluoroacetic anhydride (19.5 g), was added 9 g of 3-[1-allyl-3-(2,6-dimethylphenyl)-thioureido]propionic acid. The reaction mixture was stirred at 0°-5° C. for 4 hours, then stirred at ambient temperature for 72 hours. The reaction mixture was poured into ice-H2O, basified with saturated NaHCO3 solution, and extracted with methylene chloride (100 mL). The organic phase was dried over anhydrous magnesium sulfate, then evaporated to a gum. Purification was achieved by flash chromatography on silica gel (9:1=CH2Cl2 :MeOH). Crystallization from hexane afforded the title compound (4.2 g) as a white solid, m.p. 88°-91° C.

Workup

  1. stirringstirred at ambient temperature for 72 hours
  2. extractionextracted with methylene chloride (100 mL)
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customevaporated to a gum
  5. customPurification
  6. customCrystallization from hexane

Sources & evidence

ORD record
ord-095d1dce34d24bc0b5d0df606a960b85
Source dataset
uspto-grants-1998_09
Patent number
US05807864

Reaction notes

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