Pentafluorophenol → HCID 58981207, compound

HRID 1623052Notes

Reaction equation

HRID 1623052 reaction equation
[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([OH:20])=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1.[F:21][C:22]1[C:27](O)=[C:26]([F:29])[C:25]([F:30])=[C:24]([F:31])[C:23]=1[F:32].Cl.C(N=C=NCCCN(C)C)C>C1COCC1>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([O:20][C:27]2[C:26]([F:29])=[C:25]([F:30])[C:24]([F:31])=[C:23]([F:32])[C:22]=2[F:21])=[O:19])=[CH:13][CH:12]=3)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 13041PentafluorophenolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12147834HCID 12147834, compound

Product 1

HCID 58981207HCID 58981207, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.38 g (23.78 mmol) of the acid 20 were suspended in 100 ml of THF. 5.25 g (28.54 mmol) of pentafluorophenol and 5.47 g (28.54 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC*HCl) were then added. The mixture was stirred at RT for 15 h, after which the solvent was removed i.v. and the residue was partitioned between 300 ml of a sat. solution of NaHCO3 and 300 ml of ethyl acetate. The solids were filtered off through kieselguhr and the residue was washed twice with in each 100 ml of ethyl acetate. The phases were separated and the aqueous phase was extracted twice within each case 100 ml of ethyl acetate. The combined organic phases were washed with 200 ml of a sat. solution of NaCl and then dried with MgSO4. After the solvents had been removed i.v., the residue was chromatographed on silica gel using heptane/ethyl acetate 1:1. 4.7 g (46%) of the pentafluorophenyl ester 55 was obtained.

Workup

  1. customafter which the solvent was removed i.v
  2. customand the residue was partitioned between 300 ml of a sat. solution of NaHCO3 and 300 ml of ethyl acetate
  3. filtrationThe solids were filtered off through kieselguhr
  4. washthe residue was washed twice with in each 100 ml of ethyl acetate
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted twice within each case 100 ml of ethyl acetate
  7. washThe combined organic phases were washed with 200 ml of a sat. solution of NaCl
  8. dry with materialdried with MgSO4
  9. customAfter the solvents had been removed i.v
  10. custom, the residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-d608ccc4f0e1467fb7ee0cb4484ce28b
Source dataset
uspto-grants-2014_07
Patent number
US08778955B2

Reaction notes

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