Triethylamine → t-butyl 2-[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl](methyl)amino]-2-oxoethylcarbamate

HRID 2374822Notes

Reaction equation

HRID 2374822 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[CH:25]1[C:35]2[CH:34]=[CH:33][C:32]3[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=3[C:30](=[CH:40][CH2:41][CH2:42][NH:43][CH3:44])[C:29]=2[CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[CH:25]1[C:35]2[CH:34]=[CH:33][C:32]3[CH:36]=[CH:37][CH:38]=[CH:39][C:31]=3[C:30](=[CH:40][CH2:41][CH2:42][N:43]([CH3:44])[C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:29]=2[CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9918NorcyclobenzaprineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 59853902t-butyl 2-[[3-(5H-dibenzo[a,d][7]annulen-5-ylidene)propyl](methyl)amino]-2-oxoethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

105 mg (0.60 mmol) of t-butoxycarbonylglycine, 111 mg (0.58 mmol) of 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride, 133 mg (0.51 mmol) of 3-(5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methyl-1-propanamine and 0.08 ml (0.57 mmol) of triethylamine were stirred in 5 ml of dichloromethane at room temperature overnight. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture. After extracting with dichloromethane, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (hexane:ethyl acetate=2:1) to obtain the title compound.

Workup

  1. extractionAfter extracting with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by the silica gel chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-c3fdff6448b0420caf941d8d95aafad1
Source dataset
uspto-grants-2008_12
Patent number
US07462630B2

Reaction notes

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