Triethylamine → HCID 67349738, compound

HRID 910582Notes

Reaction equation

HRID 910582 reaction equation
ON1C(=O)CCC1=O.C(N(CC)CC)C.Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH2:22]([C:29]1[C:30](=[O:37])[NH:31][NH:32][C:33]=1[CH:34]([CH3:36])[CH3:35])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:22]([C:29]1[C:30](=[O:37])[NH:31][N:32]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:33]=1[CH:34]([CH3:35])[CH3:36])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 80170N-HydroxysuccinimideHCID 673516914-Benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one

Product 1

HCID 67349738HCID 67349738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Hydroxysuccinimide (1.06 g) was dissolved in tetrahydrofuran (10 g) at room temperature. Triethylamine (0.936 g) and ethyl chloroformate (1.00 g) were added to the solution successively. After stirring the reaction mixture at room temperature for 30 minutes, 4-benzyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one (2.00 g) was added to the mixture at room temperature. After the reaction mixture was stirred at room temperature for 13 hours, the reaction mixture was stirred at 50° C. for 6 hours. The insoluble materials were removed, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1) to give 4-benzyl-1-ethoxycarbonyl-1,2-dihydro-5-isopropyl-3H-pyrazol-3-one.

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 13 hours
  2. stirringthe reaction mixture was stirred at 50° C. for 6 hours
  3. customThe insoluble materials were removed
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-096bef241be745008c3f90ba77613bc3
Source dataset
uspto-grants-2011_09
Patent number
US08022192B2

Reaction notes

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