N,N,N',N'-Tetramethylazodicarboxamide → HCID 67072227, compound

HRID 1242360Notes

Reaction equation

HRID 1242360 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[N:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH2:19]([O:21][C:22](=[O:35])[C:23]([O:26][C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][C:28]=1[CH3:34])([CH3:25])[CH3:24])[CH3:20].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>C1COCC1>[CH2:19]([O:21][C:22](=[O:35])[C:23]([CH3:25])([O:26][C:27]1[CH:32]=[CH:31][C:30]([O:16][CH2:15][C:12]2[N:13]=[N:14][C:9]([C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:17])[F:18])=[CH:8][CH:7]=3)=[CH:10][CH:11]=2)=[CH:29][C:28]=1[CH3:34])[CH3:24])[CH3:20]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935719HCID 21935719, compound

Product 1

HCID 67072227HCID 67072227, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.170 g (0.669 mmol) of the above prepared [6-(4-trifluoromethyl-phenyl)-pyridazin-3-yl]-methanol and 0.163 g (0.684 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) were dissolved in 8 ml of abs. THF and treated successively at 0° C. with 0.162 g (0.800 mmol) of tributylphosphine and 0.139 g (0.804 mmol) of N,N,N′,N′-tetramethylazodicarboxamide. The cooling bath was then removed and stirring continued for one night. The reaction mixture was then poured onto crashed ice, extracted twice with AcOEt, washed with water, and dried over sodium sulfate. Evaporation of the solvents i. V., followed by flash chromatography (SiO2, hexane/AcOEt=7/3) yielded, after recrystallisation from hexane/AcOEt, 0.208 g of a colorless solid.

Workup

  1. dissolutionwere dissolved in 8 ml of abs
  2. customThe cooling bath was then removed
  3. waitcontinued for one night
  4. additionThe reaction mixture was then poured
  5. extractionextracted twice with AcOEt
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvents i
  9. customyielded
  10. customafter recrystallisation from hexane/AcOEt, 0.208 g of a colorless solid

Sources & evidence

ORD record
ord-e01095799a8148a5862f2dee70140623
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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