Trifluoroacetic acid → HCID 9863201, compound

HRID 985766Notes

Reaction equation

HRID 985766 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([S:19][CH3:20])[CH:13]=2)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[H-].C([SiH](CC)CC)C>>[CH2:1]([C:9]1[CH:10]=[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:26])[CH3:25])[C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[C:14]([S:19][CH3:20])[CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 9950905HCID 9950905, compoundHCID 131724811HCID 131724811, compound2×

Product 1

HCID 9863201HCID 9863201, compound

Procedure

A solution of the product obtained in Example 6 (2.06 mmol) in trifluoroacetic acid (20.6 mmol) is brought to 0° C. and then triethylsilane hydride (6.18 mmol) is added dropwise. Stirring is carried out at ambient temperature for one week and a fourth equivalent of triethylsilane hydride is then added. The reaction mixture is stirred for 24 hours more and is then hydrolysed and extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is chromatographed on silica gel (eluant: acetone/toluene/cyclohexane 30/50/20) and is then recrystallised twice from toluene to yield the title product in the form of a white solid.

Workup

  1. customis brought to 0° C.
  2. waitis carried out at ambient temperature for one week
  3. stirringThe reaction mixture is stirred for 24 hours more
  4. extractionhydrolysed and extracted with ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue is chromatographed on silica gel (eluant: acetone/toluene/cyclohexane 30/50/20)
  9. customis then recrystallised twice from toluene

Sources & evidence

ORD record
ord-be110c068a784d0791bc0d5339dc77f9
Source dataset
uspto-grants-2005_03
Patent number
US06872851B1

Reaction notes

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