Formic Acid → HCID 59437100, compound

HRID 2272863Notes

Reaction equation

HRID 2272863 reaction equation
FC1[C:7]([OH:8])=C(F)C(F)=C(F)C=1F.C(N=C=NCCCN(C)C)C.C(O)=O.[N:27]1([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32][CH2:31][NH:30][CH:29]([C:33]([O:35][CH3:36])=[O:34])[CH2:28]1.C(N(CC)CC)C.Cl>CCOCC.C(Cl)Cl>[CH:7]([N:30]1[CH2:31][CH2:32][N:27]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:28][CH:29]1[C:33]([O:35][CH3:36])=[O:34])=[O:8]

Participants

9

Reactant 6

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13041PentafluorophenolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate

Product 1

HCID 59437100HCID 59437100, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of pentafluorophenol in 520 mL of anhydrous ether at 0° C. there are added in succession 49 g of 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (286 mmol) in portions and 12 mL of formic acid (312 mmol). The whole is stirred at ambient temperature for 2 hours. There is subsequently added a mixture of 32 g of 1-tert-butyl 3-methyl 1,3-piperazinedicarboxylate (130 mmol) and 18 mL of triethylamine (130 mmol) in solution in 520 mL of CH2Cl2. The whole is stirred overnight at ambient temperature. The reaction mixture is hydrolysed with an 1N aqueous HCl solution and extracted with CH2Cl2. The organic phases are subsequently combined and then washed with a saturated aqueous NaHCO3 solution and then with a saturated aqueous NaCl solution until neutral. After drying over MgSO4, filtration and concentration to dryness, the product is isolated by chromatography over silica gel (petroleum ether/AcOEt gradient: 0-30%). The title product is obtained in the form of an oil.

Workup

  1. additionThere is subsequently added
  2. stirringThe whole is stirred overnight at ambient temperature
  3. extractionextracted with CH2Cl2
  4. washwashed with a saturated aqueous NaHCO3 solution
  5. dry with materialAfter drying over MgSO4, filtration and concentration to dryness
  6. customthe product is isolated by chromatography over silica gel (petroleum ether/AcOEt gradient: 0-30%)

Sources & evidence

ORD record
ord-900c232675314750a4844688e045fc7b
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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