Trifluoroacetic acid → 2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one

HRID 1755099Notes

Reaction equation

HRID 1755099 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:40][CH2:39][C:18]2([N:22]=[C:21]([C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([O:33][CH2:34][CH2:35][CH:36]=[CH2:37])[CH:24]=3)[NH:20][C:19]2=[O:38])[CH2:17][CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:34]([O:33][C:25]1[CH:24]=[C:23]([C:21]2[NH:20][C:19](=[O:38])[C:18]3([CH2:39][CH2:40][NH:15][CH2:16][CH2:17]3)[N:22]=2)[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=1)[CH2:35][CH:36]=[CH2:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668182902-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester

Product 1

HCID 668171362-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (27 ml) was added to a solution of 2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester (2.39 g, 5.12 mmol) in methylene chloride (54 ml), and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was concentrated under reduced pressure with azeotropic distillation with toluene, and the resulting residue (trifluoroacetate) was then dissolved in methanol (50 ml). A 4 N solution of hydrochloric acid in dioxane (16 ml) was added and the mixture was concentrated under reduced pressure. The resulting residue was dissolved in a mixed solution of ethyl acetate (100 ml)-ethanol (5 ml), followed by washing with a 1 N aqueous K3PO4 solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (1.92 g). This compound was used in the next reaction without further purification.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure with azeotropic distillation with toluene
  2. dissolutionthe resulting residue (trifluoroacetate) was then dissolved in methanol (50 ml)
  3. additionA 4 N solution of hydrochloric acid in dioxane (16 ml) was added
  4. concentrationthe mixture was concentrated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in a mixed solution of ethyl acetate (100 ml)-ethanol (5 ml)
  6. washby washing with a 1 N aqueous K3PO4 solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ec6d612c1b4d4e3eb6d3ff76d7ac4dd8
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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