Triethylamine → HCID 67141134, compound

HRID 1864441Notes

Reaction equation

HRID 1864441 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=O)[C:14](=O)[N:13]=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.[B-](F)(F)(F)F.CN(C([O:53]N1C(=O)C=CC=C1)=[N+](C)C)C>CN(C)C=O>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([N:31]2[CH2:30][CH2:29][N:28]([C:22]3[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:21]=3[CH3:20])[CH2:33][CH2:32]2)=[O:18])[CH2:14][NH:13][C:12]1=[O:53])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 705421-(2,5-Xylyl)piperazine2×HCID 2733204O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium TetrafluoroborateHCID 67141147HCID 67141147, compound

Product 1

HCID 67141134HCID 67141134, compoundYield 435.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-(−)-oxo-1,5-imidazolinedicarboxylic acid 1-benzylester (10 g) and 1-(2,5-dimethylphenyl)-piperazine (7.92 g) in N,N-dimethylformamide was added O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N,N-tetra-methyluronium-tetrafluorborate (TPTU) (12.36 g) and triethylamine (15.8 mL), and the reaction mixture was stirred at ambient temperature over night. Additional amounts of the reagents were added, 1-(2,5-dimethylphenyl)-piperazine (1.44 g), TPTU (2.25 g) and triethylamine (2.9 mL), and stirring was continued until no starting material could be detected. The solvent was evaporated and the residue redissolved in ethyl acetate/1M aqueous solution of Na2CO3. The inorganic phase was extracted with ethyl acetate and the combined organic phases were dried (Na2SO4), filtered and evaporated. Purification by column chromatography (SiO2, dichloromethane/methanol 95:5) yielded (S)-5-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-2-oxo-imidazolidine-1-carboxylic acid benzyl ester (14.4 g) as a white solid. MS: 435.3 ([M−H]−)

Workup

  1. additionAdditional amounts of the reagents were added
  2. customThe solvent was evaporated
  3. dissolutionthe residue redissolved in ethyl acetate/1M aqueous solution of Na2CO3
  4. extractionThe inorganic phase was extracted with ethyl acetate
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by column chromatography (SiO2, dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-fc8c34f064a742b59651912f93e6ddaa
Source dataset
uspto-grants-2009_12
Patent number
US07625902B2

Reaction notes

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