Trifluoroacetic acid → HCID 67629372, compound

HRID 1598454Notes

Reaction equation

HRID 1598454 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23]C(C)(C)C)=O)[C@@H:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:32][C:33]1[C:41](C)=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](O)=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.C(N(CC)CC)C.CN(C)C=O>[CH2:8]([N:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:23])[C:41]2[CH:40]=[CH:39][CH:38]=[C:34]([CH3:35])[C:33]=2[CH3:32])[C@@H:17]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 117822,3-Dimethylbenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60009260HCID 60009260, compound

Product 1

HCID 67629372HCID 67629372, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
20 °C

Procedure

Trifluoroacetic acid (4.5 mL) was added to a solution of 4-benzyl-1-tert-butoxycarbonyl-2(S)-n-butylpiperazine (0.507 g, 1.52 mmol) in methylene chloride (9 mL), and the reaction stirred for 2 h at 20° C. The volatiles were removed in vacuo and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The crude product was dissolved in dry, degassed dimethylformamide (18 mL) and 2,3-dimethylbenzoic acid (0.229 g, 1.53 mmol), HOBT (0.222 g, 1.45 mmol), and EDC.HCl (0.307 g, 1.60 mmol) added. The pH was adjusted to 8 by the addition of triethylamine. The reaction was stirred at 20° C. overnight, and the dimethylformamide removed in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was washed with saturated sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo to give the title compound.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. dissolutionThe crude product was dissolved
  6. customin dry
  7. additionadded
  8. stirringThe reaction was stirred at 20° C. overnight
  9. customthe dimethylformamide removed in vacuo
  10. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  11. washThe organic phase was washed with saturated sodium chloride solution
  12. dry with materialdried over magnesium sulfate
  13. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8fc2ca7d11244a508bc1b668f589012d
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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