Trifluoroacetic acid → HCID 12017817, compound

HRID 990379Notes

Reaction equation

HRID 990379 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13]([N:15]1[CH2:20][CH2:19][N:18]([CH:21]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:17][CH2:16]1)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:7][C@@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C:13]([N:15]1[CH2:16][CH2:17][N:18]([CH:21]([C:29]2[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=2)[C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:19][CH2:20]1)=[O:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 54172469HCID 54172469, compound

Product 1

HCID 12017817HCID 12017817, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-(1-{4-[Bis-(4-fluoro-phenyl)-methyl]-piperazine-1-carbonyl}-3-methyl-butyl)-carbamic acid tert-butyl ester (7.30 g, 14.6 mmol, Example 50) was dissolved in CH2Cl2 (50 mL) under nitrogen at ambient temperature. To this solution was added trifluoroacetic acid (12 mL). The resulting reaction mixture was stirred for 50 minutes, then concentrated in vacuo. The viscous pale-amber oil obtained was mixed with 50 mL of saturated aqueous NaHCO3 solution and stirred for 10 minutes, 50 mL of CH2Cl2 was then added. The resulting mixture was stirred until bubbling ceased. The two layers were separated, organic layer was successively washed with saturated aqueous NaHCO3 solution (2×50 mL), brine (2×50 mL), and was dried over Na2SO4. The solution was concentrated in vacuo affording 5.92 g (92%) of the pure titled compound as a off-white foam: mp 61-68° C. APCI-MS m/z 402.3 (MH+);

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customThe viscous pale-amber oil obtained
  4. stirringstirred for 10 minutes
  5. stirringThe resulting mixture was stirred
  6. customuntil bubbling
  7. customThe two layers were separated
  8. washorganic layer was successively washed with saturated aqueous NaHCO3 solution (2×50 mL), brine (2×50 mL)
  9. dry with materialwas dried over Na2SO4
  10. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ec85bf4ca63043829a437a887a733f0c
Source dataset
uspto-grants-2002_10
Patent number
US06458781B1

Reaction notes

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