Trifluoroacetic acid → HCID 11037161, compound

HRID 977234Notes

Reaction equation

HRID 977234 reaction equation
O[CH:2]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)[CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>O>[CH3:10][C:9]1[O:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][C:5]=1[CH2:4][CH2:3][CH2:2][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 11761871HCID 11761871, compound

Product 1

HCID 11037161HCID 11037161, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-[3-[4-[1-hydroxy-3-(5-methyl-2-phenyl-4-oxazolyl)propyl]phenyl]propyl]-2,4-oxazolidinedione (0.14 g), triethylsilane [(C2H5)3SiH] (0.075 g) and trifluoroacetic acid (2 ml) was stirred at room temperature for 3 hours. The reaction mixture was poured over water, neutralized with an aqueous solution of sodium hydrogen carbonate and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure; the residue was purified by silica gel column chromatography. From the fraction eluted with chloroform-methanol (100:3), 5-[3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propyl]phenyl]propyl]-2,4-oxazolidinedione (0.11 g, 82%) was obtained, which was then recrystallized from ether-methanol to yield colorless needles having a melting point of 119°-120° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. washFrom the fraction eluted with chloroform-methanol (100:3)

Sources & evidence

ORD record
ord-80a8f4829fe64243a57c3bbb819a9d02
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

Loading…