Triethylamine → HCID 59853884, compound

HRID 2374843Notes

Reaction equation

HRID 2374843 reaction equation
C([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]([N:17]1[CH2:22][CH2:21][C:20](=[C:23]2[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[CH:27]=[CH:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]2=3)[CH2:19][CH2:18]1)=[O:16])[C:10]([O:12][CH3:13])=[O:11])=O)(C)(C)C.Cl.C(OCC)(=O)C.C(N(CC)CC)C.[C:52](Cl)(=O)[C:53](C)([CH3:55])[CH3:54].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O>[CH:33]1[C:28]2[CH:27]=[CH:26][C:25]3[CH:34]=[CH:35][CH:36]=[CH:37][C:24]=3[C:23](=[C:20]3[CH2:19][CH2:18][N:17]([C:15](=[O:16])[CH2:14][CH:9]([NH:8][C:6](=[O:5])[C:53]([CH3:55])([CH3:54])[CH3:52])[C:10]([O:12][CH3:13])=[O:11])[CH2:22][CH2:21]3)[C:29]=2[CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 59853907HCID 59853907, compound

Product 1

HCID 59853884HCID 59853884, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

600 mg (1.19 mmol) of methyl 2-[(t-butoxycarbonyl)amino]-4-[4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-piperidinyl]-4-oxobutanoate was dissolved in 5 ml of ethyl acetate. 0.5 ml of 4 N hydrochloric acid/ethyl acetate solution was added to the obtained solution, and they were stirred at 0° C. for 3 hours. After stirring at room temperature overnight, the solvent was evaporated under reduced pressure. The residue was dissolved in 10 ml of dichloromethane. 602 mg (5.95 mmol) of triethylamine and 158 mg (1.31 mmol) of pivaloyl chloride were added to the obtained solution, and they were stirred for 10 minutes. Saturated aqueous sodium hydrogencarbonate solution and water were added to the reaction mixture. After extracting with ethyl acetate 3 times followed by the drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane:ethyl acetate=89:11 to 65:35) to obtain the title compound.

Workup

  1. stirringAfter stirring at room temperature overnight
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 10 ml of dichloromethane
  4. stirringwere stirred for 10 minutes
  5. extractionAfter extracting with ethyl acetate 3 times
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by the silica gel chromatography (hexane:ethyl acetate=89:11 to 65:35)

Sources & evidence

ORD record
ord-47d6415bbe204e7b979a1bdb4debeccc
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

Loading…