Trifluoroacetic acid → HCID 54312597, compound

HRID 2280519Notes

Reaction equation

HRID 2280519 reaction equation
[C:1]([N:24]1[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]1)(=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22].C(C(O)=O)(F)(F)F.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[N:24]1([C:1](=[O:23])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:21][CH3:22])[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 67493435HCID 67493435, compound

Product 1

HCID 54312597HCID 54312597, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of tert-butyl 4-docosa-4,7,10,13,16,19-hexaenoylpiperazine-1-carboxylate (1.5 g, 3 mmol) in CH2Cl2 (20 mL) at 0° C. was added CF3CO2H (7 mL, 91 mmol). The mixture solution was stirred (0° C., 2 h) and then 10% Na2CO3 was added to adjust pH=10. The mixture was extracted with CH2Cl2 (3×30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography (CH2Cl2: CH3OH, 20:1) to afford 1-(piperazin-1-yl)docosa-4,7,10,13,16,19-hexaen-1-one (1.17 g, 97.5%) as a colorless oil. Mass calculated for C26H40N2O=396.61. found: [M+H]+=396.7, 398.2.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica chromatography (CH2Cl2: CH3OH, 20:1)

Sources & evidence

ORD record
ord-bb3186f445174260a41b6bebd13ee590
Source dataset
uspto-grants-2015_09
Patent number
US09139516B2

Reaction notes

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