Trifluoroacetic acid → HCID 69386370, compound

HRID 916846Notes

Reaction equation

HRID 916846 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:16]=[CH:17][CH:18]=1)(C(C)(C)C)(C)C.C(O)(C(F)(F)F)=O>C1COCC1>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([NH:19][C:20]([NH2:22])=[O:21])[CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 69386115HCID 69386115, compound

Product 1

HCID 69386370HCID 69386370, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[3-(4-{[tert-butyl(dimethyl)silyl]oxy}butyl)phenyl]urea (5.67 g) in THF (50 ml) was treated with TFA (13.56 ml) and stirred at room temperature for 1 h. Further TFA (5 ml) was added and the reaction mixture stirred for a further 16 hours. The reaction mixture was concentrated in vacuo. The residue was co-evaporated with methanol and then suspended in methanol and heated at reflux for 20 h prior to concentration in vacuo. The residue was purified by chromatography (SPE, DCM-MeOH 9:1) to give the title compound. LCMS RT=2.14 min.

Workup

  1. stirringthe reaction mixture stirred for a further 16 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. temperatureheated
  4. temperatureat reflux for 20 h
  5. concentrationto concentration in vacuo
  6. customThe residue was purified by chromatography (SPE, DCM-MeOH 9:1)

Sources & evidence

ORD record
ord-2f85b272aa224d369b752b298c987d14
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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