Imidazole → HCID 59897690, compound

HRID 1841623Notes

Reaction equation

HRID 1841623 reaction equation
Cl.C(OC(=O)[C@H](C)N[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)C1C=CC=CC=1.N1C=CN=C1.C(N1C=CN=C1)(N1C=CN=C1)=[O:33].C(NCCN(C)C)CC(C)C.[CH2:55]([C@H:62]([NH:72][C:73]([N:75]([CH2:81][CH2:82][N:83]([CH3:85])[CH3:84])[CH2:76][CH2:77][CH:78]([CH3:80])[CH3:79])=[O:74])[CH2:63][O:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)C1C=CC=CC=1>O1CCCC1.C(Cl)(Cl)Cl>[CH2:65]([O:64][C:63]([C@@H:62]([NH:72][C:73]([N:75]([CH2:81][CH2:82][N:83]([CH3:85])[CH3:84])[CH2:76][CH2:77][CH:78]([CH3:80])[CH3:79])=[O:74])[CH2:55][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:17][CH:18]=1)=[O:33])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

8

Reactant 5

HCID 795ImidazoleHCID 682631,1'-CarbonyldiimidazoleHCID 16770624HCID 16770624, compoundHCID 69882164HCID 69882164, compoundHCID 69882515HCID 69882515, compound

Product 1

HCID 59897690HCID 59897690, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 4-biphenylyl-L-alanine benzyl ester hydrochloride (270 mg) in anhydrous tetrahydrofuran (2 ml), there were added imidazole (50 mg) and 1,1′-carbonyl diimidazole (155 mg) in the nitrogen gas atmosphere and the resulting mixture was stirred at room temperature for 10 minutes. Then a solution of N-isopentyl-2-(dimethylamino) ethylamine (Reference Compound 2-2, 589 mg) in anhydrous tetrahydrofuran (3 ml) was added to the mixture, followed by the reflux with heating for 1.5 hour. Chloroform was added to this reaction liquid under ice cooling, the reaction liquid was washed with saturated sodium hydrogen carbonate aqueous solution and then with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting oily product was purified through the silica gel column chromatography to give the title compound (Compound 4-1, 402 mg).

Workup

  1. temperaturereflux
  2. temperaturewith heating for 1.5 hour
  3. customthe reaction liquid
  4. washwas washed with saturated sodium hydrogen carbonate aqueous solution
  5. dry with materialwith saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting oily product was purified through the silica gel column chromatography

Sources & evidence

ORD record
ord-336fb3df06c641aba2c8d651d3004606
Source dataset
uspto-grants-2004_01
Patent number
US06683200B2

Reaction notes

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