Triethylamine → HCID 86585547, compound

HRID 1454149Notes

Reaction equation

HRID 1454149 reaction equation
[C:1]([O:5][C:6]([N:8]1CCC(CN)CC1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([CH2:22][CH2:23][CH2:24][CH:25]([CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]([OH:28])=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O[N:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=N1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:44][CH2:45][CH2:46][CH2:47][C:42]1([NH:41][C:26](=[O:28])[CH:25]([CH2:24][CH2:23][CH2:22][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:43][NH2:39])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21892253HCID 21892253, compound

Product 1

HCID 86585547HCID 86585547, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Butoxycarbonyl-4-aminomethylpiperidine (51) (0.30 g; 1.4 mmol) is dissolved in DMF (10 mL) at ambient temperature. 5-Phenyl-2-(3-phenyl-propyl)-pentanoic acid (22) (0.415 g: 1.4 mmol) is added followed sequentially by 1-hydroxybenzotriazole (0.2364 g; 1.75 mmol), triethylamine (0.2439 mL; 1.75 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.2952 g; 1.54 mmol). The mixture is stirred at ambient temperature for 18 hours then poured onto ethyl acetate (300 mL) and extracted sequentially with water (100 mL), 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL). The organic layer is dried (MgSO4), filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography with gradient elution (10%→50% ethyl acetate in hexanes) affording the desired compound (0.67 g) as a colorless oil. ESMS: MH+ 493.4

Workup

  1. additionthen poured onto ethyl acetate (300 mL)
  2. extractionextracted sequentially with water (100 mL), 1N HCl (50 mL), saturated NaHCO3 (50 mL), and brine (50 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified via silica gel chromatography with gradient elution (10%→50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-74fe56ba5ad544d9bbec12fb91041f05
Source dataset
uspto-grants-2009_01
Patent number
US07476680B2

Reaction notes

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