Acetic Acid → HCID 54170807, compound

HRID 1872570Notes

Reaction equation

HRID 1872570 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH:5]1[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][Si](C(C)(C)C)(C)C)[CH:20]=2)[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]1=[O:18].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH:5]1[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:25])[CH:20]=2)[C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12][C:11]1=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 18408714HCID 18408714, compound

Product 1

HCID 54170807HCID 54170807, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[N-(2-hydroxyethyl)piperazinyl]-5-[3-(tertbutyldimethylsilyloxy)phenyl]barbituric acid (170 mg) in 12 ml of tetrahydrofuran, kept at 0° C. and under nitrogen atmosphere, are added 333 μl of acetic acid and 0.69 ml of tetrabutylammonium fluoride. The mixture is stirred for 3 hours then the solvent is evaporated off and the residue is purified by silica gel chromatography (15 g; eluent: ethyl acetate/methanol 4:1), to give, after crystallization from methanol, 35 mg of the product, m.p. 219-221° C.

Workup

  1. customkept at 0° C. and under nitrogen atmosphere
  2. customthe solvent is evaporated off
  3. customthe residue is purified by silica gel chromatography (15 g; eluent: ethyl acetate/methanol 4:1)
  4. customto give
  5. customafter crystallization from methanol, 35 mg of the product, m.p. 219-221° C.

Sources & evidence

ORD record
ord-0551edc9badf4b919e4cb4b4245f1353
Source dataset
uspto-grants-2000_08
Patent number
US06110924

Reaction notes

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